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A moan claws its way up Dean’s chest, spilling out without his permission.“Daddy…” he’s gasping for air, every nerve-ending feeling as if they’re on fire. “Daddy, Imma…”“You can hold it, sweetness,” Daddy says calmly. Way too calmly. Motherfucker.He’s hard as iron, filling Dean in the best of ways, the slide aided by a generous amount of lube and the fact that Daddy ate him out before pressing gently inside him. Daddy knows intimately that Dean responds well to being pounded hard, but he also knows what really makes Dean lose his mind. Namely getting fucked real slow while his whole body convulses with pleasure.And Dean loves that Daddy knows that and delivers perfectly but damnit, he really needs to come right now!His dick is so hard it’s aching, bobbing between his legs with Daddy’s slow and measured thrusts and how the fuck can he be so damn controlled right now?! Dean doesn’t know, but he does get off on Daddy not losing his cool even when he’s at the brink of coming. No, Daddy usually keeps his composure and it makes Dean feel safe and it’s so fucking hot how Daddy is skilled enough to turn Dean into a babbling mess without even ruffling his carefully tailored suit.One of Dean’s favorite times having sex is in Daddy’s office, between meetings. His fantasy is that Daddy has to take a call while ramming Dean and not missing a fucking beat. But he hasn’t told Daddy that yet and this is anyhow not the time.Right now they’re both naked, which is all kinds of hot, and Dean is pressed down on Daddy’s bed, Daddy between his legs and sliding his hot and hard cock in and out of Dean’s greedy hole.The bedroom in Daddy’s fancy apartment is softly lit with only a single lamp on a dresser opposite the bed and Dean loves the way the light plays over Daddy’s tantalizing body. He’s so fucking hot, hair wild and skin taut over toned muscles.And his cock, fucking hell…It fills Dean like no one else’s, pressing in all the right ways and reaching all the right spots. Dean was a goner already the moment he first saw Daddy across the crowd in his friend Charlie’s internet café but after seeing his cock he knew he wouldn’t—couldn’t!—ever look back.And now just look at him. Over a year later and still crying out his orgasms, hanging off of Daddy’s cock.“I-I…”It’s dribbling out of him now, with every push Daddy makes. Daddy’s hands are big, huge, on Dean’s slim hips and all the sensations make Dean tremble with arousal.“I’m close, darling,” Daddy growls, his usually rumbly voice going scratchier the closer he comes to release. Dean fucking loves it. “Hold it.”Dean can’t, he absolutely can’t. He can feel it, gathering in his tight balls, the pleasure burning in his groin, his whole body feeling electric as the come forces its way out of him, his mind going blank.He makes a kind of gargling, embarrassing sound, trying to warn Daddy, and there’s not much else he can do. The pleasure crests in a way it only does with Daddy, and Dean arches his back, eyes rolling back, toes curling, and there he fucking goes.His hole clenches hard around Daddy’s cock, in time with the spurts that shoot out of him, coating his stomach, and he feels a thrill go through him when Daddy grunts and stills. That means he’s coming inside Dean and Dean’s so fucking ecstatic about it that he can barely think.“Oh, sweetness,” Daddy says softly, lovingly, and Dean’s breath stutters out of him. “So perfect for me.”Dean’s whole body shudders and he whimpers, reaching for Daddy with heavy arms, movements sluggish as residual pleasure pumps through him. Daddy complies, gathering Dean in his strong arms, cocooning him in Daddy’s warmth and strength, his cock still lodged in Dean’s hole. He clenches around the older man when they kiss and Daddy groans into the kiss.It’s sweet, the aftermath. Dean is not very used to it but he secretly loves it. He has a lot of sex but nothing quite like this. It’s draining in all the best of ways and Dean is pliant when Daddy—Cas—gently cleans off his body with a damp washcloth.Dean looks at how happy Cas looks doing that for him. How Cas, Castiel Novak, architectural business tycoon and eligible bachelor number one on Forbes’ list three years in a row, seems the most content taking care of his partner. It makes Dean shiver with pleasure when he thinks about him being Cas’ partner for now. Cas is handsome and kind, wealthy and intelligent, but also a little nerdy and cute as fuck and in moments like this Dean feels damn lucky to have landed Cas as a sugar Daddy.He lets out a happy sigh when Cas strokes his big hand up Dean’s inner thigh, close to his groin.“Damn, Cas,” he murmurs, smiling when he meets Cas’ dark eyes. “You’re really my number one Daddy.”He freezes as soon as the words are out of his mouth, staring down at Cas with wide eyes. Cas is smiling, clearly pleased, but what the actual fuck? What compelled him to say that?! “Thank you,” Cas murmurs.It’s not wholly untrue and the thought has been growing inside him for a while, months, but it’s also so fucking stupid to say shit like that.“No, I mean, um,” Dean sits up on his elbows, mind whirring.“I know what you mean,” Cas chuckles, a very pleasant sound. He leans in, gripping Dean’s chin gently and stealing a quick kiss. “But one day it’ll be true, sugar pie. I will be number one for you.”The cocky confidence, the absolute assertiveness, the energy born from years of leading other people. It laces Cas’ every word and fuck, if Daddy hadn’t fucked Dean so good he was as wrung out as the washcloth, he would be sporting a goddamn boner right now. His dick sure tries to fill out and he feels Daddy’s eyes on him, licking his body.He breathes out shakily, looking up at Daddy with hooded eyes. “Yeah?” he asks, tone clearly indicating a challenge because Dean is a dumbass who can’t control himself. “Yes,” Daddy concludes and arousal shoots down Dean’s spine. Fuck.But also no! Dean has to shake himself. What the fuck is he even doing challenging Cas to become his number one sugar Daddy? He’s very happy being a professional sugar baby to his four Daddies, thank you very much.All the comforts of sex and presents and none of the complications of actual relationships and love. He gets enough of love from romantic movies or the boys love Mangas Dean pretends he doesn’t devour with fervor.It’s because Charlie keeps recommending him the books, and sometimes giving him her copies, and what the fuck is he supposed to do when his best friend does something so sweet for him? Refuse to read them? Rude. And Mangas are so easy to read anyway. A whole book takes less than an hour and Dean has a lot of free time on his hands that he has to fill with something. Anyway, the point is that Dean isn’t looking for love and Cas knows that. Maybe Cas just means to monopolize Dean’s time but that wasn’t what they arranged from the beginning. Dean would be loath to break it off with Cas, who is objectively the best sugar Daddy—no, what he means is that Cas is great. His cock is great. So yeah, Dean doesn’t want to lose that but if Cas won’t respect the rules they set from the beginning, he needs to cut him off.“Relax, sweetness,” Cas says then, almost as if he can hear Dean’s racing thoughts. Or as if Dean’s carefully constructed poker face is suddenly shit. Cas leans in to kiss Dean again, even quicker this time, and Dean’s lips tingle pleasantly from the contact. “I’m only teasing you.”Oh. Dean chuckles a little nervously. Good. Cas doesn’t want to be his number one Daddy, he’s only teasing Dean. That swooping feeling in the pit of Dean’s stomach isn’t disappointment, shut up. It’s because he sat up too quickly. And also relief. Yeah. “That’s good,” Dean chirps, rolling off the bed and skipping over to the luxurious bathroom in Cas’ penthouse apartment. “Now c’mon, let’s shower.”“Yes,” Cas murmurs. “Good.”It’s an hour later when Dean finally leaves, but only because Cas insisted on fixing Dean a meal before allowing him out of the apartment. Cas is good like that, providing top-notch aftercare and Dean is grateful for it, even if he playfully banters with Cas about it. “You’re spoiling me,” Dean will say and Cas will only smile and nod. “I’ll grow fat and ugly from all the good food,” Dean will joke and Cas will kiss him deeply and tell him that he’ll be beautiful in all shapes and forms.Cas is good at that too; at making Dean feel appreciated and loved.Dean sighs as he stands in the elevator, riding it down, away from Cas. Loved. Guess Cas really put ideas in his head tonight. He looks himself over in the mirror in the elevator, inspecting his neck and collarbones for marks. Two of his sugar Daddies like to mark him up, although it feels different when Cas does it. Better, maybe, but Dean isn’t about to say that out loud, not when Cas has already been spouting possessive nonsense.Today there aren’t any marks and Dean smiles at his reflection. No marks but he looks damn delicious in skinny, white-washed jeans, a tight tank top and an oversized bomber jacket. All of his clothes are of the best quality, mostly haute couture, anything to make him appear like the definition of a high-end twink and a real professional sugar baby. He pinches his lower lip just as the elevator doors slide open, puffing it up, and pulls out a pair of sunglasses from his jacket pocket. He slides those on top of his head, smiles flirtily at the concierge, who only grins back, and struts out of the penthouse building. He is supposed to pick up his little brother Sam in less than half an hour so he heads directly to where he parked his precious car. It’s a vintage ‘67 Chevy Impala that Cas bought him after Dean went bananas for it. Dean and Sam’s dad used to have one just like this, but of course in worse condition, since everything they owned when dad was still alive had been in shit condition. Sure, dad had done his best and he’d managed to save up enough to send at least one of them to college for a semester before he’d succumbed to gastric cancer. His life insurance had covered some more but at this point Dean is the one providing for Sam so that he can continue on his college dreams at Stanford in California. Well, in essence it’s Dean’s sugar Daddies providing for them, but same diff. Dean’s the one running around pleasing four men to get what he wants and needs. There’s Michael, who owns a heap of clothing stores and who keeps Dean and Sam clothed with expensive labels and quality fashion. There’s Ketch, who has a successful restaurant chain that works with top chefs like Gordon Ramsey and who never lets Dean and Sam go hungry. There’s Crowley, who owns too many apartment complexes to count and who has put Dean in one of the best apartments, only outshined by Crowley’s own penthouse, of course.And then there’s Cas, who’s so ridiculously rich off family wealth and successful businesses, who turns everything he touches into gold, and who gives Dean everything he could ever want. What Dean even needs after being so thoroughly provided for by his other Daddies he doesn’t know, but he’d decided to nab Cas the second he laid eyes on him.He’d come into Charlie’s café, hair wet from the rainstorm outside and eyes curious as they darted around, taking in everything in the café from the plush couches by the bookcases to the computer stations to the nerd-themed pastries by the counter.To be fair, a lot of the patron’s in the café had been interested in Cas but Dean, being the absolutely fabulous professional he is, had been the quickest to react. And now look at him, cruising through the nightlife of San Jose, flipping off the hipsters who get upset at the sight of his gorgeous gas-guzzler, high on life and on top of the world after getting so thoroughly fucked he kind of forgot the time.Well, it’s not like Sam’s gonna be too mad if Dean’s only a few minutes late. He is supposed to be at what his friends call a party, and what Dean calls a dork convention, having the time of his life. Lord knows he fucking needs to relax sometimes with all the studying he’s doing. Dean will never know how he does it, the second-hand stress he receives from just watching Sam’s mounting homework is enough, thank you.Sam seems to thrive, though, and that’s all that Dean cares about. They are all the family that’s left now, since dad left this world, and Dean’s keen on keeping his little brother happy. That’s why, even though Sam has a room at the Stanford dorms with his friends, Dean always keeps a room available in the apartment Crowley pays for. Sometimes, on nights like this, it’s easier to bring Sam home than to the dorms and sometimes Sam just needs a break. Or somewhere to bring a girl, but that has happened less frequently since he started his third year of pre-law. Dean supposes Sam has too much to focus on now, and he kind of feels bad for his baby brother, even though he is proud as fuck of him.The address Sam has texted him leads Dean to another complex, this one with studio apartments with an industrial theme. It’s not a place he has been before and not where Dean expected to find his baby brother but whatever, Dean’s not perturbed by a change in scenery. Fuck knows his Daddies surprise him often enough that he’s come to expect it. The elevator is less fancy than in Cas’ building but that’s no shock. Everything is less fancy than Cas’ stuff. It’s bumpy and creaky and Dean eyes the panel over the doors that slowly tick up the numbers. It flickers ominously on floor 6 but passes it just fine, bringing him to floor 8 without trouble.In the hallway it’s not difficult to figure out which door the party is behind and Dean is actually surprised no neighbor has called the cops because whew, that’s loud. He frowns his way over, ignoring the way the fluorescent lights buzz overhead. Ringing the doorbell of course gives no answer because who the fuck can hear it over the deep techno bass playing inside? He tries the doorknob instead and finds it open, which makes his skin prickle. Dean has done a lot of shit in his life but he was hoping Sam wouldn’t find his way into half of it. Partying in an unfamiliar apartment with the door unlocked in a seedier part of Redwood seems like a bad beginning. Inside the apartment it’s dark, with only a few lamps throwing long shadows, or the shadows creeping over what little light the lamps provide. Dean sucks on his teeth, a nervous habit he won’t admit to, and makes his way into the depths of the darkness. In the living room he finds a group of people, not the usual dork squad Sam normally hangs out with, and Dean is less than pleased about that fact.Sure, he’s guilty of making fun of Sam and his friends a lot but it’s all in good fun, since he actually likes Sam’s friends very much. They remind him of Charlie, smart and funny and safe. Someone dependable. He can tease Sam all he wants about only having law dorks for friends but the fact is that his own best friend is an IT and popular culture nerd and he fucking loves her. The people in this room give off a different aura altogether and Dean towers over their stoned and drunk forms, arms akimbo and a displeased expression marring his delicate features. He knows he shouldn’t judge based on their appearance, especially since he is frequently judged himself, and he’s really not. He’s judging the situation on the vacant, unfocused look in their eyes, the dopey grins, and the fact that no one has noticed him, a stranger, in the room.Well, Sam notices quick enough and Dean’s happy about that at least.“Dee!” he exclaims and heaves himself off the couch, smiling widely and weirdly. “Hey everybody, it’s my brother Dean!”Everybody cheers, but Dean doubts they know what they’re cheering for. “Sam,” he says and uses the voice he adopted when they were younger and dad had to leave Dean in charge for the day. The almost-dad voice. “Having fun, are we?”Sam cringes a little. Good, Dean thinks. Truth be told, Dean’s not above recreational drug use but he had hoped Sam would know better than to do it with people he doesn’t know. Or does he know them? Dean squints at the people in the room. No, they’re all new faces, at least to him. “I was,” Sam says and snakes his arms around Dean, pulling him into a hug and nuzzling his face against Dean’s neck. “Ruby showed me stuff.”Dean hopes it’s only recreational drugs… “Ruby, is it?” Dean murmurs but before he can put his arms around his little brother, a perky woman bounds up to them, eyes gleaming.“That would be me,” she announces proudly, grinning. “Are you really Dean? The way Sam talks about you I’d thought you’d be cooler.”Dean levels her with a flat stare. “I’m exactly as cool as I need to be, missy.”Her expression instantly sours but fuck if Dean cares about that. She has obviously introduced Sam to something more than alcohol and Dean doesn’t like it. Doesn’t like the way Sam clings to him, not because he doesn’t like to hug his brother but because Sam isn’t clingy, not normally. “You look like a pretty flower,” one of the guys on the couch says in a rough voice. Dean’s skin crawls when the guy looks him up and down. “Pretty rude,” Ruby mutters.Dean huffs and turns to pull Sam out of there. “Well, you all have a good night.”No one stops them and Dean’s happy for it, even though it’s a bit concerning how no one seems to care that Sam is more or less being dragged out of there. He supposes it can be because Sam announced Dean as his brother and decides to go with that explanation since it makes him feel better. In the car, Sam leans his forehead against the passenger side window and sighs.“Rough party?” Dean asks when they’re halfway home and the silence is stifling him. Sam takes a moment longer to answer but he’s not asleep, Dean can see the reflection of his open eyes in the window.“It was fun,” Sam says then but his tone, oh there’s something in his tone. “At first.”Dean sucks on his teeth again. “Tell me.”Sam shakes his head but he continues anyway. “Ruby, she’s different at uni. More, um…”“Calm?”Sam winces. “I thought she was cool,” he says and his voice is low. They stop at a red light and Sam straightens in his seat. “I was, uh, enthralled.”Typical Sam, using all decorative language like that. “You were horny,” Dean corrected. “I’m gay but I’m not stupid, she’s hot.”Sam looks like he’s floundering for a moment. “Her body is hot.” He sneers at himself, ever the feminist, but Dean doesn’t think there’s anything wrong in admitting someone looks good. But then he gets it, gets why Sam is ashamed.“You don’t like her as a person.” He states and starts driving again when the light turns green. Sam looks as if Dean piecing it together is the surprise of a century. “So you feel bad about sleeping with her.”“I didn’t—how’d you—” he deflates and Dean purses his lips so he won’t smirk at his little brother’s struggle. “You always were better with the mind games.”Dean shrugs. “It’s not like I haven’t done that too.” He doesn’t look at Sam when he says that, pretends he needs to look at the road really hard right now. Sam is more than aware of what Dean does to pay for everything and he has never liked it, but he has never condemned Dean for it either. “But hey, there’s nothing wrong with a little mindless, meaningless sex once is a while,” he slaps Sam on the shoulder. “You need it, dork.”“Yeah…” Sam says slowly.“I’m more concerned with what you have been doing all night,” he makes a gesture. “Pills? Alcohol?”Sam shakes his head vehemently. “Just some weed, Dee. I swear.”Cute, Dean thinks, how Sam is definitely an adult, well into his twenties and a hot shot pre-law student, but he still reacts like a kid sometimes. “Okay,” Dean says and chooses to believe Sam. He has never had any reason not to before. “Guess I was just a bit unnerved finding you in that apartment, with people I don’t know.”“I don’t know the rest of them either,” Sam mumbles and then, in an even lower voice. “I think they heard me with Ruby.”Ah, so the shame isn’t only about mindlessly fucking a girl he doesn’t really like, it’s also about a bunch of seedy guys maybe listening in. Dean wishes he’d gotten there sooner, even though he technically hadn’t been late. “Relax, Sammy,” he says encouragingly just as they drive into the garage under the apartment complex Dean lives in. “College is for making mistakes like some slightly illegal and morally questionable shit, right?”“I guess,” Sam mutters.Truth be told, Dean isn’t really sure what exactly Sam is upset about. The sex? The drugs? The people he doesn’t know? Had he expected something different when he went to Ruby’s house? Maybe he had thought it was a date, but then why had he told Dean he was going to a party with friends? Dean squints, guiding his precious car carefully through the garage. Had he, though? Had Sam really said “with my friends”? Hadn’t it been more like, “I’m going to a party”? Dean doesn’t know why the distinction would matter, except now he feels bad for not listening properly, and for assuming.In any case, Sam had fun and then he didn’t, and now he’s probably coming down from the high and that’s not hitting him well. Some people deal with that better than others, after all, so Dean doesn’t say much about it.Instead he leads Sam up to his apartment, keys them in, helps his little brother out of his clothes and into the bed he always has prepared for him in the spare bedroom. He puts painkillers and some water on the nightstand, kisses Sam’s forehead, and leaves the door slightly ajar, the hallway light on.How reminiscent of when they were younger and dad worked the graveyard shift. Or later, when Sam didn’t need Dean as much but dad did because he was so sick. Dean does and doesn’t like it at the same time. Likes being needed, feeling useful, but wishes it was about something else. Even though it’s late, he prepares a sandwich for himself and eats it standing in front of the big windows in the living room, looking out at the city below. It’s dark, with only a few lights twinkling here and there and Dean feels powerful standing over it and looking down. Like Batman on his perch.His phone chimes in his pocket, breaking the silence, and Dean almost gets annoyed before he sees that it’s from Cas.It reads a simple Get home okay? and Dean can’t help but smile. He shoots off a text, confirming it and gets a smiley in return. For someone so suave, Cas sure likes to use emojis, which is a fact Dean thinks he should find lame but that he actually finds cute as fuck.He doesn’t answer that lone smiley, though, but instead goes to his calendar to check his schedule. With four Daddies he’s had to resort to partial scheduling and so far no one has complained. Well, it’s not like he never sees them outside of their allotted days, so he supposes that contributes to keeping everyone happy. He feels disappointment for a scant second when he sees that it’ll be a few days until he will meet with Cas again, unless he changes stuff around or makes a surprise appearance. That disappointment is firmly squashed, though. Because no matter what Cas had said tonight about being Dean’s number one Daddy, that’s not the case and it won’t ever be.A shiver goes through him, his eyes growing heavy when memories of their last fucking comes to mind. Cas is cocky for a reason, that’s for damn sure.He trails the tips of his fingers down his throat, feels the pulse there and imagines it’s Daddy Cas doing it to him. Daddy with his long and clever fingers, playing Dean’s body like a violin. He’s way too good at that, as if all of Dean’s erogenous points are clearly marked for Daddy to find. Marked by a glowing X, he goes from one to another like a damn blood hound and Dean fucking loves it. The shell of his ear, just above his clavicle, his nipples, below his belly button nosing down to his hips and the base of his dick. Yeah, Cas sure as fuck knows just the right way to go to turn Dean into a moaning mess. He shudders now, realizing that he’s standing there with his eyes closed in front of the large windows and touching every point on his body that Cas mapped out just hours earlier. And it’s turning him on something fierce. A sudden desire to jerk off right then and there washes over him but he stops himself at the thought of Sammy waking up and catching him in the act. Instead, he goes to his bathroom, undressing quickly and getting under the hot water in the shower. The pressure is divine and it takes the water no time to heat up, the facilities in Crowley’s apartment complexes nothing but perfect.Pouting to himself as he rubs his wet hair, he forces thoughts of Crowley out of his mind. He’s a good sugar Daddy and all but he’s not what Dean likes to think about when he pleasures himself. Not that he should be thinking about any of his Daddies when he’s alone, that would only lead down roads filled with dark and dangerous temptations. Being a sugar baby is like a job for Dean and that’s how he wants it. No feelings, no strings, just pleasure, money, and comfort.That being said he also forces Cas out of his mind, even though he had been the one to start this fire in Dean tonight, for the second time. Instead he conjures up images of good-looking actors and other faceless men with nice hands and cocksure smiles, and takes his dick in hand to easily stroke himself to full hardness. It doesn’t go all too well after that. Well, the hardness and the pleasure part goes fantastic. Arousal licks up and down his body, making his nipples pebble, and when he touches them, he has to bite his lip to silence a needy whimper.But keeping his Daddies out of his mind goes bad as fuck. Keeping Cas out is an especially big disaster. Usually after getting fucked by Cas, Dean doesn’t have to resort to self-pleasure. Usually, he’s completely satisfied and fucking hell, he had thought this night was the same as always. But Cas had opened his inviting mouth and said that. Said that he wanted to be Dean’s number one, and now Dean’s mind is all jumbled.Where the fuck had that even come from? Dean doesn’t know and refuses to admit that it was actually him who said it first.When all his usual tricks fail, he falls back to his original jerk off routine, the one that had started the exploration of his young body all those years ago. The three famous Rs.Ryan Gosling, Ryan Phillippe, and Ryan Renolds. Yes, the three Rs never fail him and as he stands there in his shower, fantasizing about being tended to by the three handsome actors, his mind finally fizzes out and he’s free to surrender to pleasure.Leaning his back against the cool tile wall, he tilts his head back, gasping when his dick hardens impossibly more. One hand down between his spread legs, he rubs below his tight balls, down, down, over his perineum. He’s a little sore from the fucking he just took so he avoids his hole but fuck it feels good to rub the sensitive skin on his taint.That damn whimper escapes now anyway, all without Dean even noticing, so lost in how tight everything feels. Ryan is kneeling in front of him, prepared to suck him off as he comes, and Ryan is behind him, supporting him, and Ryan stands to the side, leaning in to kiss his neck. Dean moans, turning his head, eyes tightly shut, body shuddering. He comes hard a handful of strokes later and as always, the Ryans disappear the moment he does. Dean doesn’t care about that, though, too caught up in the pleasure as he releases right into the shower stream. It all washes away as soon as it pumps out of him and Dean is happy for it. Personally, he likes to masturbate in bed better, simply because it’s more comfortable and he tends to get spaghetti legs after and it’s difficult to keep standing, but he can’t deny the easy cleanup of a shower jerk.Scrubbing himself quickly with some of the expensive soap Daddy Michael buys for him, he ignores the feeling that this hadn’t even been a percentile as satisfying as when Cas fucks him. It was good enough and besides, he’d been pretty damn fucked out already so that’s probably why. It was a goddamn miracle that he’d even gotten hard enough to need to jerk off, to be honest. Drained, he smiles the moment he comes into his spacious bedroom and sees his bed. It’s a huge, king sized monstrosity that has no business being that big since Dean never brings a bed partner here. Well, sometimes Charlie sleeps over when their movie nights drag on and instead of sleeping in the extra bedroom like Sam, she shares Dean’s bed. Dean likes that, likes sleeping beside another living, breathing body.He has considered getting a pet for that very reason but doesn’t think he has it in himself to care for it. It’s enough to keep himself afloat while he cares for Sammy. Tonight he doesn’t think about anything like that, though. Tonight he’s simply grateful to see his bed, its soft covers and fluffy pillows inviting him like a lover’s embrace.

----- CHAPTER BREAK -----

Dean’s morning routine usually consists of having some kind of shake for breakfast and then about an hour in the gym or the pool, depending on his mood. Not because he particularly enjoys either one, would frankly rather have bacon for breakfast every day, but because he believes it’s smart to keep in shape as a sugar baby. People of course have different opinions on what beauty is but objectively Dean thinks he’s considered above standard and wants to keep it that way. Having regular workouts and semi-healthy food certainly contributes, he thinks. Because let’s face it, Dean is financially dependent on his sugar Daddies and out of all of them, only Cas has promised to love Dean no matter what he looks like.Dean makes a face as soon as the thought enters his mind. Love. It’s the next day and Dean still can’t shake Cas’ words of devotion from his mind. He feels ridiculous and takes it out on himself by forcing himself to do so many laps in the pool that his body feels like lead by the end of it and he can barely get out of the water. After a shower and a cookie he feels better, ready to take on the world, and he is just about to pick his outfit for the day when Sam stumbles into Dean’s bedroom, looking tousled and sleepy.“Good morning,” Dean says brightly, just to be an ass. Sam is clearly hungover and Dean is no stranger to that feeling. “Ready to tackle classes today?”Sam grumbles and hugs himself. “Why are you always so perky in the morning?”Many reasons, actually. He’s used to getting up early and taking care of Sam and dad, his sugar Daddies sometimes want to meet in the morning and expect nothing but the best from him, and also sometimes Dean battles with insomnia. Thoughts of dad’s last months alive, combined with intense longing and hatred for the mother that abandoned them when Sam was a baby all mingle with the moral battle he fights every time he thinks about the fact that the way he approaches being a sugar baby is not much different from being a whore. It sometimes adds up to a cocktail of emotions that won’t let him sleep and in those cases he might as well get up and do something productive with his day.On days like this, though, it’s more because he has stuff scheduled early in the day and he slept like a baby so he’s feeling energized. He usually sleeps well after a session with Daddy Cas but that’s neither here nor there. “Because I like to torment you, of course,” he smirks and holds up two shirts. “Which one?”Sam makes a face as if he’s smelling something bad. “None, they’re too gaudy.”Dean nods, looking down at the shirts. “I know, but Michael likes me to stand out.”“Likes you to…” Sam shakes his head, clearly uncomfortable and Dean wonders not for the first time if it was a mistake to tell Sammy about his sugar Daddies. Well, mostly Sam had figured it out by himself because he’s too damn smart for his own good, but still. “Go with the green one.”“Because it matches my eyes?” Dean asks jokingly, jostling the shirt. It’s made from silk and barely makes a sound. “I guess,” Sam mutters. “I dunno what your men like to see you in.”Ah, so the uncomfortableness seems to mostly be about Sam not liking to dress his brother in clothes that make him the most fuckable. That makes sense, Dean thinks as he slips on the shirt, since he doesn’t particularly like to think about Sammy having sex either. The material is cool in his skin and he looks good in it, he thinks as he looks himself over in the mirror. Behind him, Sam is still hugging himself, looking young and tired, enough so that Dean takes pity on him.“Why don’t you stay here today?” he says, voice soft and soothing. “Skip classes, sleep in. There’s food in the fridge and you can always have stuff delivered.” He turns, going over to his brother and running his fingers through his hair. “The cleaning lady doesn’t even come in today, so no one will bother you.”You’re safe here, is what he’s trying to say, but words of comfort and feelings are hard. Better to be practical about it. Sam gives him a pinched smile. “Don’t, I deserve to suffer. Who even parties on a school night?”Such a nerd thing to say, Dean thinks fondly. “College students?” he suggests teasingly. “Seriously though, no one’s gonna chew you out for missing one day.”He turns back to his clothes, pulling out a pair of Corduroy hotpants. Michael’s thing is thighs, and Dean certainly knows how to deliver. “Feels cowardly if I don’t go…”“You mean because of Ruby?” Dean asks without looking at Sam, busy choosing accessories like the diamond earrings Michael bought him. “You know it’s kinda lame to be playing games like that.”“You play games all day long.”Dean turns to Sam but doesn’t see the judgmental expression he expected, instead Sammy looks a little contrite, as if he hadn’t meant to say that out loud. Dean cocks his head to the side but Sam doesn’t say anything more.“That’s for work,” Dean concludes, smiling when Sam nods, looking down. “But anyway, you decide on your own. You have your key.” He walks past Sam, headed for the hall. “I need to go. You can call me if you need anything but I might not hear you,” he throws a flirty grin over his shoulder. “I’m going to a fashion show.” ***** Truth be told, Dean has a few errands to run first. Dry cleaning to pick up, a fitting for a business suit Daddy Crowley has ordered for him, and Michael wants to meet for brunch before the fashion show. Dean isn’t really a brunch guy at heart but he certainly doesn’t mind being treated to a nice bowl of pretentious tomato soup.“After this, we’re heading to the venue,” Michael says, his hand landing on Dean’s thigh under the table. “It’s only a small thing, just a few designers from Milan. Oh, and Joanne. You like Joanne, don’t you, baby?”“Yes, Daddy,” Dean purrs, having no fucking clue who Joanne is. Presumably a designer or model or something of the sort but Michael brings him to a flurry of parties and Dean doesn’t have the interest to keep everyone’s name in mind. “I’m very excited.”“Good,” Michael says smugly and proceeds with talking a bunch of nonsense about clothes and fashion that doesn’t interest Dean in the slightest.Oh he will listen and ask all the appropriate questions and he’s not having a bad time per se, but would he rather be holed up at home playing video games in his underwear and eating burgers for breakfast, lunch, and dinner? Yes, of course. But since Dean approaches being a sugar baby like a job, and he is nothing if not dedicated, he will sit here and smile interestedly all day.The venue they go to after brunch is indeed small but man is it gaudy, even more so than what Sam had thought of Dean’s shirts. In contrast, Dean feels underdressed now and he regrets asking his little brother for advice. Sam dresses mostly in jeans and t-shirts anyway, what does he know?Well, Daddy seems to appreciate Dean’s clothes well enough anyway, judging by the way he keeps groping Dean’s thighs during the fashion show. Dean is okay with PDAs but it feels excessive. Perhaps it’s because Daddy is so invested in the show and forgets himself. Thankfully it’s dark enough where they’re sitting in the audience, all of the lights on the thin models strutting on the runway, showing off clothes no one in their right mind would wear. Dean thinks he will never get fashion, but then again he doesn’t have to.He just has to sit here and feign interest while looking pretty and not think too much. Not about the tv show he wants to watch or about Cas and how much more fun it is with him. How, when Dean is out with Cas, nothing really feels tedious and Dean—He cuts off his own thoughts hard. Damn, Cas really did a number on him yesterday and it’s not even the first time he has mentioned really liking Dean. But to want to be Dean’s number one Daddy, that’s new. New enough that Dean can’t stop thinking about it, apparently.“That’s something for you,” Daddy Michael suddenly murmurs and Dean forces himself to focus on the model that’s walking past them right now. “You would look so precious in that.”Dean can’t even wrap his head around what it is he’s looking at. A dress? A pantsuit? Is it even clothes? It’s just straps and cloth and okay, he does like the color. A demure purple, or lavender if Dean had known more colors than just the basic ones, so he smiles at Daddy.“It’s pretty.”That earns him a new squeeze to his inner thigh and Dean thinks this date will probably end in sex. Not all of his dates with his Daddies do, not all of the time, and it’s more frequent with some of them than others. Like with Cas. With him it happens every time and Dean still can’t get enough.He squeezes his eyes shut for a moment, gritting his teeth. What he wouldn’t do to not be a dumbass, but apparently that’s not the hand he was dealt. Well, he was also dealt a stubbornness that thankfully gets him through the rest of the fashion show without further stray thoughts and afterwards there’s a party that seems way too excessive for a regular midweek afternoon but hey, Dean doesn’t complain when he gets handed a glass of chardonnay. Truth be told, he kind of needs the alcohol at this point, even if he would have preferred one of Cas’ bourbons. The afterparty is held in what looks like a conference hall and Dean is actually surprised. It’s much less extravagant than the venue for the fashion show and seems more of a budget place, not somewhere he is used to being with Michael. The thought seems to have struck Daddy too and his mood sours somewhat.“Try these canapes, Daddy,” Dean chirps, hugging Michael’s arm and holding up a canape with what looks like some kind of pâté. “They’re good.”Michael relents at Dean’s sweet tone and allows himself to be fed, holding Dean’s eyes as if what they’re doing is something sexy, and as if they’re alone and not in a room surrounded by Michael’s colleagues and fashion designers. There are even some of the models floating around the periphery, now thankfully in more normal clothes. Dean would have pitied them if they’d had to wear what they had showcased on the runway.“So this is where you’re hiding,” an old man says, coming upon them just as Dean is about to feed Michael another canape. He grins and Dean smiles cutely back, stuffing his face with the canape instead. “In the shadows with this pretty thing.”Dean squirms, hugging Michael’s arm again, preening for this man like he knows Michael enjoys because Daddy likes to show off his “pretty things”. “I’m hardly hiding,” Michael chuckles even though that was precisely what they were doing, mostly since Michael is unhappy with what he perceives as a shabby afterparty. He’s spoiled, like that, and Dean kind of resents him for it but hides it well enough.“Daddy is protective,” Dean mumbles, taking a chance and looking up at the man through his lashes. “I’m shy.”The man looks taken aback but Dean isn’t worried that he made an error in judgment. Sometimes when he’s out with one of his Daddies, he refers to them by name in front of other people, since not everyone will be okay with someone being a sugar baby or Daddy, but Dean has gotten pretty apt at judging the situations over the years and has learned that some people most definitely responds very well to it.This case is no exception and the man looks Dean up and down before turning a leer on Michael. “How kind of you,” he grins and Michael smirks in return, clearly happy with the attention. As if having Dean as his sugar baby gives Michael some kind of higher status, puts him on a pedestal to be admired. Well, Dean can kind of admit that that’s a rush for him too, since most people wouldn’t think like that if he hadn’t looked like some kind of prize to them, but mostly he thinks it’s ridiculous. Michael literally pays Dean to stay with him, it’s not like Michael is anything special beyond that. Some Daddies are, of course, but Dean is definitely not thinking about anyone in particular.“So,” Michael starts with an air of superiority, addressing the man with his back straighter. “What did you think of the show?”It’s some long couple of hours before they finally leave the afterparty and Dean is tipsy from too little food and too much chardonnay so he gratefully tumbles into Michael’s limo, guided by Daddy’s strong hands.“Mh,” Dean hums, nuzzling up to Michael as soon as they’re inside the limo and moving away from the party. “That was fun.”“Yeah,” Michael murmurs and presses a button that slides up a black partition to hide them from the driver. “Did you have a good time, baby?”Dean hums again, body pleasantly loose when Michael pulls him into his lap. He moans into their first kiss of the evening, arms snaking around Michael’s neck as they grind lazily together. As usual, Michael’s body is quick to respond and if Dean is being honest he’s feeling pretty fired up too right now. Michael is a good-looking guy and he’s nice to Dean, if a little possessive at times, and with Dean’s wayward thoughts of late and the alcohol in his system, he feels pretty damn invested in this make-out session.“Everyone was staring at you, baby,” Michael growls, groping Dean’s ass, fingers sliding up his hotpants. “You’re so pretty.”Dean moans again, his poor dick aching to be let out of his clothes. His erection is almost hampered by the shorts and it’s a delicious kind of hurt, like a cockcage, even though he would rather just whip off his clothes and have his lover worship his body. But that isn’t the kind of guy Michael is in bed and Dean knows that. Knows what to expect and it’s fine, it’s good enough.“I only wanna be pretty for Daddy,” he mumbles and looks shyly at Michael, play-pretending a bit as they rock together, aided by the limo’s movements. “You are,” Michael groans. Dean can feel his dick jumping and fuck yeah, Dean wants that inside him. “Such a sweet baby boy.”Okay truth be told, Dean is very into calling his lover Daddy but being called a baby boy is a bit too much for him. Still, it doesn’t deter him right now and he eagerly opens up for Michael when he kisses Dean deeply. It’s sloppier now, more heated, and by the time the limo stops outside Michael’s apartment complex Dean is so tightly strung he’s practically vibrating.They laugh a little about it, Michael looking like he was caught with his hand in the cookie jar, and they both have to adjust themselves before exiting the limo. The driver smirks at Dean behind Michael’s back but Dean just ignores him and hides in Daddy’s big suit jacket so that his boner isn’t too much on display. Because it’s one thing to look pleasantly flushed and another to conduct public indecency. They grind together as soon as they’re alone in the elevator, the perceived privacy giving them a false sense of comfort and Dean loses himself a little in the motion. Michael smells fairly good, at least his cologne does, and he’s a nice kisser. Less hungry and owning than Daddy—than Cas, but good enough. Sometimes, when Dean can’t help it, he kind of takes over a little with Michael, directing the way they have sex and Michael seems to like that a whole lot, which is not something that Dean looks for in his partners but it’s fine.At least Michael’s dick is good enough. Not quite the cock Dean’s ass craves, but a nice shape and girth nonetheless, and Dean is anyhow the kind of cockslut that likes any and all dicks as long as they’re attached to a decent person and Michael, for all his shortcomings, is more than decent towards Dean.The main problem that usually arises during sex with him is that he’s too quick on the draw, and as he shudders against Dean in the elevator, Dean starts suspecting that’s where they’re headed tonight as well. Fuck, Dean is so horny he knows he needs to come and Daddy better deliver or Dean’s going to become one pouty brat in the morning.“You’re so fucking sexy,” Michael growls just as the elevator stops and the doors ding open.They stumble out into a thankfully empty hallway and Dean giggles attractively, gluing himself to Daddy’s side as they walk stiffly up to his penthouse door. Both of them are obscenely hard but neither care now, so close to the actual privacy of Michael’s lavish home. Too lavish, some might say, gaudy Sam would definitely say, his new favorite word in Dean’s mind. But Dean doesn’t care how it looks since he doesn’t have to live there. It has a good bed, nice shower, and Michael has no problem letting Dean use either. It’s a good place to get a nice dicking and Dean sure as fuck hopes that’s where this will end. With a dick in his ass until he screams out his orgasm and ruins the sheets.Unfortunately that’s not exactly what happens. Instead it’s what Dean feared and as soon as Michael gets his dick in Dean’s ass he groans loudly and starts pumping like a fucking piston. No enticing rolling, no regard for Dean’s prostate or dick or body, just a complete and feral use of a hole and sure, Dean likes feral, likes being a ragdoll for Daddy, but there is a lack in finesse that Dean thinks Michael will never learn.“So fucking tight,” Michael grunts, hips smacking against Dean’s ass and Dean wants to think it’s pleasurable but it’s mediocre at best. “My baby boy.”To be honest the most pleasure Dean gets is when Michael presses him down so that Dean’s dick grinds against the bed. And okay, Dean will come like this but will it be as fulfilling as he knows it can be? Hardly. Maybe he shouldn’t be thinking about that right now, though. Shouldn’t be thinking about other sex with someone else when he’s being plowed by Michael.But he’s drunk and horny and he can’t help it. Can’t help how his mind wanders, remembers strong hands and confident touches, remembers blue eyes and kisses that make his whole body yearn for more. Remembers the latest orgasm and fuck, fuck, it pushes him over the edge now.“Daddy!” he moans loudly, of course not thinking about Michael.Michael grunts again and comes as soon as Dean’s ass starts milking him and Dean thinks hazily that this might be the first time he came before Michael since they started having sex. And it’s all Cas’ fault. ***** Later when Dean gets home — because fuck if he was spending the night after imaging Cas during sex with Michael — he finds his apartment empty save a note from Sam that he will read later. Because right now he has a few choice words to say to Cas.
1:03 a.m. [Me]:    u made me fuk up    don do that
He blinks at the phone and makes an annoyed sound at the back of his throat. He’s more sober now, the thing that happened helping, and the cold air he got while riding the cab to his apartment with the window down, but he’s apparently not sober enough to make sense. Better turn on autocorrect for this shit.Irritated, he sets out to try again when he sees Cas typing. Damnit, he was supposed to be asleep and read this in the morning! Damn night owl, that one.1:04 a.m. [Cas]:    You’ll have to elaborate on that 🤔That fucking emoji… Dean wants to chuckle and squirm and fall into the couch to text with Cas and his stupid emojis all night. But no! He needs to set boundaries! He does snuggle up on the couch, though, wedged in the corner between the armrest and back, facing the big windows and the black night sky.
1:04 a.m. [Me]:    I *mean* you put stuff in my head    I’ve never thought of another Daddy when I have sex with one
Probably shouldn’t have said that… That’s bound to put ideas in Cas’ head and that’s the opposite of what Dean needs right now.1:05 a.m. [Cas]:    And you mean to tell me that you did now? 👀
1:05 a.m. [Me]:    I don’t mean anything no more
Shouldn’t have said anything. What did Dean hope to accomplish by this conversation to start with? Well fuck it, he’s still tipsy and he’s annoyed. Granted it’s mostly with himself but it’s not like he’s about to admit that.1:05 a.m. [Cas]:    Tell me true now, sweetness ❤Fuck.“Don’t call me that now,” Dean mumbles into the empty room, feeling his body stir. That fucking petname of Cas’…
1:05 a.m. [Cas]:    Who did you think about when you let another Daddy fuck you?
He shouldn’t do it, shouldn’t admit to how much Cas has affected him. How what he said a whole day ago still lingers on Dean’s mind and how he imagined Cas’ sure touches all night when he was with Michael and his fumbling.
1:06 a.m. [Me]:    You
Dean’s heart lodges in his throat. First at the sight of that lone word that he apparently sent without thinking about what the fuck he was doing and then again the second after when his phone screen lights up with an incoming call from Cas.“Don’t pick up,” he mumbles to himself even as he swipes to accept the call. “Don’t indulge.”Good advice, surely, but not enough to keep him from moaning “Daddy” into the phone as soon as the call connects.“Are you lonely, sweetness?” Daddy all but growls and Dean lets out a whimper, sinking lower on the couch and pressing a hand between his legs. Arousal is already coursing through him and he would feel blindsided by how fast it came if he had the wherewithal right now. “Are those other men not enough for you?”Dean doesn’t want to talk about that right now. He puts the call on speaker phone and puts his other hand between his legs as well.“Wanna see you, Daddy.”Daddy tuts and Dean’s whole fucking body lights on fire. “Not for a little while, sugar pie. I respect your rules.”Fuck the rules. Dean was the one to set them so if he wants to break them it should be okay, right? He moans, squirming on the couch.“Want Daddy’s touches.”“Daddy wants to touch you too,” Daddy rumbles and yes, yes, that’s how he sounds when he starts getting aroused. “Tell me what he did wrong.”Dean shakes his head but there’s no one there to see it besides his furniture and what the fuck does it matter anyway? At this point he has already broken his own rules, the ones about not talking to his Daddies about the other Daddies and this isn’t even the first time, not when it comes to Cas.“He’s too meek,” Dean moans, rubbing his dick through his tight hotpants.“Mm, yes, you want to be with someone who takes charge.”“Yeah,” Dean gasps. “Wanna, wanna lose control.”He’s about to fucking lose it right now, his dick already leaking in his pants and fuck he can’t work the zipper open. It makes him whine pathetically, to which Daddy grunts.“What’s wrong, sweetness?”“Take off my pants, Daddy,” Dean cries, bucking against his own hand. “Wanna come.”That makes Daddy chuckle and Dean might just fucking come like this. The pleasure is sharp and hot, sizzling through him and making his whole body taut and pliant at the same time.“I would peel them off you with my teeth if I was there,” Daddy says, voice a deep rumble so pleasant Dean feels it like a living thing in the room with him. “I would take your pretty dick in my mouth and suck you off.”Desperate, Dean tears open his pants, busting the button, although he won’t notice that until the morning. He gasps sharply and starts stroking himself with quick flicks of his wrist, light and fast and oh so good.“More,” he moans, one hand coming up to pinch his nipple through the sheer shirt. “Tell me more.”“You sound so good when you beg,” Daddy groans. “I would tease you; you know I like that.”“Yeah,” Dean nods unnecessarily. “I like that too.”“So good to me,” Daddy rumbles. “I would suck you while I play with your little hole. Always so eager for Daddy.”Dean can’t fucking take it anymore, he’s fucking into the tunnel of his fist, his ass clenching desperately as he wriggles on the couch.“Are you touching yourself, Daddy?” he gasps. “Are you fucking your hand too?”“You know I am, sweetness,” Daddy grunts and Dean’s mind flails wildly, desperate to see that, to be under Daddy when he comes hard all over Dean, claiming him. “I can’t listen to you like this and not get hard, no chance.”Dean whimpers, feeling his own orgasm pummeling through him. “Wanna come in your mouth.”“Daddy would love that. Love to swallow your sweet release.”Only Cas loves all of Dean this much, all his other Daddies have their personal reservations but Cas wants all of Dean, all the time, and it’s such a fucking rush.Stroking his dick slower now, dragging his orgasm out, he turns to his phone.“Would you eat me out again, Daddy?” he slurs in a sultry voice, egged on by his own arousal.“Anything you like, sugar pie,” Daddy says and sounds all deliciously breathy now. He’s close, Dean knows, and it’s so fucking hot how much he desires Dean. “I’d eat you out good, swallow everything you give me when you come, and then I’ll make you come again,” he inhales sharply and fucking fuck, he’s going to come just thinking about it, Dean is sure. “Hanging off my cock.”He growls out the last part and that’s about all Dean needs. His body goes even tauter somehow, heels digging into the couch and one hand clawing the cushions as he releases all over himself. It fucking erupts, pulling his balls up and into him, and he screams Daddy’s name as he comes hard.He lies there for a while after, panting and listening to Daddy’s breathing evening out, drawing too much comfort in how Cas sounds right as he comes and afterwards.“Cas,” he mumbles as soon as he has regained his senses and guilt washes over him. “I…I’m…”“I should be there,” Cas says when Dean is unable to continue. “I should take care of you now.”It sounds as if it mentally pains him not to be by Dean’s side and he knows from experience that Daddy Cas is huge on aftercare. Loves to wash Dean’s body after and feed him, make sure he is okay and that nothing they did went too far. Well, this time is different and they did go too far. Dean has never spoken to one of his Daddies like this outside of their sessions, their scheduled appointments, and he shouldn’t want to, has never wanted to.But something compelled him to drunk-text Cas tonight and even though whatever happened here is on both of them, Dean will take most of the blame. Because Cas is right, he is respectful and mindful of Dean’s rules and he has never contacted Dean other than for scheduling reasons.“It’s okay, Cas,” he murmurs, looking down at his ruined clothes with a scrunched-up nose. “I shouldn’t have texted.”Cas hums. “I’m glad you did.”Dean shouldn’t be but fuck if he isn’t. Not going to admit that out loud, though.“I know but like… Please forget about it?” he sighs, sitting up gingerly. “I’m just drunk and I was annoyed.”“I’m sorry I invaded your thoughts,” Cas offers, not sounding sorry at all. “I hope your other Daddy didn’t notice.”“Nah, it’s cool,” Dean swallows.He shouldn’t be talking about this either. But there’s something about Cas, something that was there even before he went and said stuff that fucked up Dean’s mind and heart. So far Cas is the only Daddy to know about the other Daddies. Well, they all know Dean has more than one and that he’s not exclusive, but Cas knows more, for some reason Dean doesn’t want to admit to.“That’s good,” Cas says and this time it sounds like he means it. Because even though he apparently has some kind of wish to monopolize Dean, he doesn’t want to actively fuck with Dean’s life. That’s good to know, Dean thinks. Although why Cas would want to monopolize Dean is beyond him. It’s not like he would want anything other than an exclusive sugar baby/Daddy contract, right?“Yeah, he was pretty drunk too and anyway, he’s usually a two-pump chump so like, it’s not unusual that… uh…” what the hell is he talking about now?!Cas’ chuckle brings Dean out of his own head. “Sorry to hear it.”“Fuck, Cas,” he groans, dragging a hand down his face. “I’m too drunk and tired and,” confused, he’s confused as fuck about what’s going on here. In all his years as a sugar baby, things have never been this complicated before. “I should go to bed.”“Sounds like a good idea,” Cas says, his voice a comforting rumble now, not the arousing kind but equally as enticing to Dean’s sense. “I’ll see you in a little bit.”“Yeah, and remember to not remember this,” Dean grumbles, to which Cas chuckles again.“I’ll try to remember.”“To not remember,” Dean adds, frowning. “Right, Cas?”“Good night, Dean.”Motherfucker, Dean grouses, looking down at the black phone screen. Guess Dean is going to have to forget twice as hard, for both of them, and hey, one time doing something like this is nothing. One time is negligible. He has to tell himself that, otherwise he’s in a heap of trouble and Dean isn’t quite ready to admit that yet.

----- CHAPTER BREAK -----

The next day Dean wakes up in a kind of euphoric state, as if he has woken to a world where everything is just perfect, and he lies for a moment, just smiling up at the ceiling. And then his memories set in and he groans, hiding his face.What the fuck had he been thinking texting Cas like that? And then taking his call?! Fuck, they’d had phone sex and that’s something Dean so far has never indulged a Daddy in because it feels too personal for him. This happened on his own time, not an appointed, scheduled Daddy session, and that makes it so much more real and Dean can’t want real. He needs and depends on all his Daddies to pay for his living and for Sammy’s tuition and everything that comes with going to college and living where they do.He can’t want real and he doesn’t want it, period.It’s just that Cas got under his skin with all his nice words and perfect touches and good looks. Cas is just a real catch is all and when he calls Dean sweetness or sugar pie or something like that Dean melts like a stick of butter in the hot Californian sun.But that’s neither here nor there because Dean is a professional fucking sugar baby and he has no problem juggling all four of his Daddies!Well, he didn’t have a problem juggling three of them but then Cas came along…Groaning again, he rolls out of bed. Maybe he should consider dropping one of them after all, just to not make his life so hectic. He’d been fine before he got Cas, although his and Sammy’s lives of course have benefited from having an extra income. Maybe he should consider dropping Cas…His whole body feels icy cold at the thought of never meeting Cas again so to compensate he jumps into a scalding hot shower, though he resolutely does not indulge his stupid dick, which tries valiantly to fill out.After that shower he goes through his normal morning routine and when it’s time for lunch he decides to swing by Stanford’s campus grounds, shooting off a text to Sammy. Usually Sam of course eats with his friends but Dean is a bit worried for him after what happened with that Ruby girl and hey, it’s not unusual that they meet up for lunch or dinner or something. Dean likes hanging out with his little brother and he thinks Sammy feels the same. It’s familiar and safe, and Dean doesn’t really experience that much with other people save perhaps Charlie and Ca—Dean grits his teeth, parking on the campus parking lot to wait for Sam to answer his text. It’s hot enough that Dean has to roll down the window and he looks out at the students he can see in the quad from here. They’re all in summer wear and Dean almost feels overdressed in his polo shirt but it’s thin enough that it’s not too hot and he’ll anyhow have to go home and change before his date with Daddy Ketch tonight. Ketch likes Dean to look more slutty than classy and Dean doesn’t mind, though he wouldn’t force his little brother to be seen with him when he is dressed to impress his sugar Daddy.An incoming text confirms that Sammy would like to have lunch together and that he’ll meet Dean in ten minutes. To pass the time, Dean texts some with Charlie, promising to come by her internet café and hang out this weekend, and then he peruses the news on his phone. And there, smack dab in all the other mundane local news, he spots one of his Daddies.Crowley is an influential real estate mogul, owning everything from apartment complexes like the one Dean lives in, to business centers. The article is about a new project of his, housing on the outskirts of Redwood, and suddenly Dean’s newly tailored suit makes sense. Crowley likes to bring Dean with him for business meetings, not because Dean is involved in anything that’s going on at them, but probably more as a distraction, or accessory.Not that Dean doesn’t want to know about what Crowley does, and not because he’s too dumb to understand, but he has simply never been afforded the opportunities to study or work with something like that. He does enjoy it, though, when Crowley brings him along, even if it’s just as a status symbol for his Daddy or to distract the clients, or even as a fucking cupbearer. It’s interesting, and different, and Crowley is one of the better Daddies in the sense that he seldom wants anything in return from Dean, aside from his company.Sometimes he will turn to Dean after a meeting, when they’re alone in the limo, and ask what Dean’s impression of a client or another was. Dean loves that, loves how Crowley listens to him and asks his opinion as if he matters more than as a pretty face. The only other Daddy to do that is Cas but let’s not fucking go there, okay?Just to show—absolutely no one since he’s alone—how much he’s not thinking about Cas, he decides to shoot off a text to Crowley.
12:17 p.m. [Me]:     Just saw the article, congrats!
There, nothing more needed. Crowley doesn’t demand Dean call him “Daddy” left and right and unlike with Cas, it doesn’t come naturally to Dean with the others.He closes his eyes, inhaling slowly, annoyance spreading inside him. Anyway. A text like this is more in line with how he talks to his Daddies outside of scheduling calls and texts, short and to the point and to be frank, Dean rarely does even this much and neither do his Daddies. Because they’re all in a business relationship and nothing else.
12:20 p.m. [Crowley]:     Thank you, it’s all going according to plan
Dean chuckles. So formal. Well, texting has never been Crowley’s preferred communication. Not like a certain someone with their emoji obsession.
12:20 p.m. [Me]:     Is this what the suit is for?

12:20 p.m. [Crowley]:     Yes. Did the fitting go well?     I should have been there with you
Because Crowley likes to micromanage, nothing else to it, although if Dean wants to read things into it, he can. He doesn’t, though, but decides to be cute about it anyway.12:21 p.m. [Me]:     It did, tho it would’ve been nicer if you were there ❤
12:21 p.m. [Crowley]:     I’m sure. See you Friday
Dean smirks to himself.
12:22 p.m. [Me]:     Yes, Daddy
He likes to banter with Crowley like this and if Dean was to pick a favorite, which he isn’t, Crowley would definitely be in the top two. Not because of sex, which is fairly infrequent with Crowley, or at least has been as of late, but because of his wit.He’s just about to go back to reading the news when there’s a new notification for an incoming text. Thinking Crowley has something to add, Dean clicks it without really looking and is momentarily startled when he sees that it’s from Cas.12:24 p.m. [Cas]:     I want you to know my sleep was ruined 😴A smile spreads on Dean’s face, warm and intimate and without his own volition or even knowledge.
12:24 p.m. [Me]:     Meanwhile, I slept like a log

12:24 p.m. [Cas]:     You’ll be the death of me
Dean’s smile widens to a pleased grin and his cheeks heat a little. Fuck yeah, Cas is affected by him, even the next day. That feels pretty fucking great, Dean’s not going to lie about that and he’s just about to text Cas back when the side door on his car opens and Sam slides into the seat, scaring the absolute goddamn daylights out of Dean.He jumps, fumbles with his phone, nearly dropping it, and turns to stare at Sam with wide eyes, only to find him smirking back.“Surprised you, did I?”“Wear a fucking bell!” Dean exclaims, locking his phone and pocketing it.Sam rolls his eyes, settling into the seat while Dean tries to calm his heart. “As if that would’ve helped. You had your nose in your phone anyway. Was it Charlie?”“Yes,” Dean lies and then immediately regrets it. “No,” he sighs. “It was Cas.”Sam knows all of Dean’s Daddies by name, though Dean has kept Sam away from them in all other senses.“Nice,” Sam says and offers a kind smile. “I like him the best out of… everyone.”Ignoring the way his heart flutters at the thought of Sam getting along with Cas, Dean turns to start up the car.“You don’t even know him.”“True,” Sam’s smile turns into the grin of a teasing little brother. “But I do know the way you talk about him, and how it contrasts with how you talk about the others.”“Shut up,” Dean mutters and pretends it doesn’t feel like his phone is burning in his pocket. “Where do you wanna eat?”“Charlie’s café has sandwiches and stuff,” Sam says as if Dean doesn’t already know and doesn’t help out in the kitchen there sometimes. “Can we eat there?”That’s the best suggestion Dean has heard in a while and he happily steers their way there, easily turning Sam to talk about his classes instead of Cas or anything dangerous like that. ***** In contrast to the relaxed lunch Dean has with his best friend and closest family, surrounded by nerd paraphernalia and engaged in fun conversations, Daddy Ketch takes Dean to the perhaps poshest restaurant this side of San Francisco and expects Dean to be thoroughly impressed.Well, in a way he is, of course, since Ketch is the owner and the restaurant seems to be doing well, with dishes that cost more per plate than some families spend for a whole week’s worth of food. It’s money like that, the kind that rich people pay without batting an eye, that in turn pays for Dean’s food through his sugar Daddy, not that that makes him more inclined to actually eat at a restaurant where he can’t even read the menu.Ketch chuckles jovially at him when Dean plays up his ignorance, and gracelessly reads the menu’s foreign language for Dean to marvel at his intelligence. Never mind that the waiter cringes behind Daddy’s back or that Dean thinks the word “vegan” should sound vaguely similar in what he assumes is Italian from the little flag on the front of the menu. Not that Dean is against eating vegan, especially since Sammy likes to encourage that, but Dean is a meat man at heart and he’s tempted to ask the waiter but of course doesn’t.With Daddy Ketch, like with Michael, Dean tends to put on a persona that’s more demure and cutely dumb which usually works in his favor but of course sometimes backfires. Like when he wants a juicy steak and has to eat some kind of grilled pointed white cabbage deal. It’s good though, and Dean supposes it’s okay since he had a rather heavy lunch. Not that he easily puts on weight or anything but he does want to watch himself since he relies on his looks for his job and at least two of his Daddies are really hung up on him being a slim sugar baby.Doesn’t stop him from ogling the dessert menu, though.“If we wrap this up, I’ll get you something good to suck on,” Daddy Ketch murmurs, leaning in to grope Dean’s ass.Dean squirms, slightly uncomfortable with such blatant physical PDAs in a place like this. Sure Ketch is the owner, but a lot of the guests around them don’t know that.“I’d like that, Daddy,” Dean mumbles, turning big eyes on Ketch. He can get himself dessert any time, after all, and he would rather get out of here before Ketch starts touching him more.They make it as far as Ketch’ town car, which isn’t as nice as Michael’s limo but still comes with a driver so that Ketch can pull Dean closer and start nibbling on him. Unlike Michael, who goes bananas for Dean’s thighs, Ketch likes to bite and knead and Dean’s body always feels like it’s been through the wringer afterwards. To please his Daddy, Dean has put on a traditionally more female blouse with a low neckline, and Ketch wastes no time latching onto Dean’s neck like a goddamn leech.He squirms and mewls like he knows Ketch like but doesn’t really feel anything himself. Not that he doesn’t like marks but Cas does it so much better. Or maybe it’s the same and Dean’s mind is just stupid about it. In any case, he turns into the rough embrace and lets Ketch manhandle him while they glide through the streets, hidden by the car’s tinted windows.A long while ago, when Dean was a new sugar baby and started considering having more than one Daddy, before he was as experienced as he is now, he was scared of marking. Not because he thinks it means much but because he was nervous his other Daddy wouldn’t like to see another man’s mark on Dean. He even lost a Daddy over it and Dean has since learned to own up to the fact that he is such a high end sugar baby that he has more than one Daddy and his Daddies will have to deal with that best they can.Surprisingly, most of them have responded well to his confidence in this case and Dean has only had to drop one Daddy a while back who was getting too possessive. Not like Cas, who is more sexy possessive, but actual stalker tendencies. That had been a bad break but Dean hasn’t had any trouble in the last couple of years and he’s very content with the four Daddies he has now. They compliment each other well in what they give him in exchange for his company and they do well to satisfy his needs.“Where did you go in your mind just now?”Oops, okay maybe some of them are less than interesting to Dean’s libido. Doesn’t mean he should let his mind stray like that while he’s with them, though…“To your bedroom,” he drawls in a sultry voice, arms snaking around Ketch’s shoulders to pull him in. “I want you, Daddy.”Ketch’s smirk is enough to convince Dean he managed to steer the situation right and they thankfully arrive at Ketch’ penthouse soon after. All of Dean’s Daddies are surprisingly similar in the way they live, in impersonal apartments and penthouses, surrounded by shiny and dead things. Dean doesn’t care, though, as long as he gets what he needs from them.Inside the penthouse, Ketch unceremoniously drags Dean over to his bedroom. Unlike with Michael, who had a certain air of desperation about him, as if he needed to be inside Dean now, Ketch acts more entitled. More like Dean is his sugar baby, therefore he will spread his legs, and Dean does so willingly, if a little apathetically. Sure, Michael isn’t what Dean would consider good in bed, but he at least makes Dean feel desired. With Ketch, Dean feels more like a dick sleeve and a roughly handled one at that.Ketch’s fingers dig into the soft flesh on the insides of Dean’s thighs and Dean grits his teeth against a hiss, quick to turn over onto his stomach on Ketch’s too soft bed. They both bounce a little and Dean face-plants, ass in the air.“Delicious,” Ketch growls, smacking Dean’s right cheek with his big hand.Dean suppresses a sigh and turns to peek back at Ketch. “Undress me, Daddy.”“Eager, are we?” Ketch chuckles and no, not really but Dean doesn’t want his clothes to rip and Ketch has a tendency to not be gentle with flimsy things like clothes.He of course doesn’t say that, though, and just moans a little. It sounds tinny and fake to his own ears but Ketch seems to respond well to it. Dean doesn’t know what the fuck is wrong with him, why this seems so difficult all of a sudden, as if he hasn’t had sex with Ketch hundreds of times already. It doesn’t mean anything, it’s just an act of carnal lust, and usually his body responds fairly well to the way Ketch has sex. He at least doesn’t come before Dean has a chance to.But tonight he just feels tired and he can’t wait until it’s fucking over. Maybe it has something to do with the fact that he came enough yesterday to satisfy him but Dean doesn't really think that’s the case since he’s a rather sexual creature. His thoughts derail when Ketch shucks off his pants. Taking a moment to get his bearings, Dean pulls off his blouse as well, while Ketch goes to get condoms and lube. Dean has already prepped himself, knowing full well that Ketch doesn’t do a good job and Dean in no way fancies having a sore ass tomorrow.He rolls to his stomach again just as Ketch climbs back on the bed and one of his big hands press against the small of Dean’s back, making him cant his ass up, arching his back with a grunt. Dean is soft for now but Ketch has never cared about that, less interested in fondling Dean’s dick and balls than he is about shoving his dick into the tight space of Dean’s ass.“Soft,” he grunts, thumbing Dean’s ass.Dean wriggles it for effect, sighing cutely. “I couldn’t help but think of you today.”“Such a slut for Daddy’s cock, aren’t we?”Dean moans out what can be interpreted as some kind of affirmative but doesn’t elaborate more than that. Not that it’s needed, Ketch’ ego is big enough for him to fill in whatever blanks he perceives. Without warning, and with less lube than Dean likes, Ketch shoves his thick thumb into Dean’s ass, groaning wildly about how tight it is. Dean tightens on instinct, against the intrusion, and has to force himself to relax so that Ketch can start moving. Dean lies there, counting backwards from 100, body jostling with Ketch’s movements and his ass yielding to the sparse prep. When he eventually lets up, after going the, for him, extended length of three fingers deep, Ketch sits back to put on the condom and Dean makes a half-hearted attempt at getting himself hard. He can feel it simmering just under the surface, Ketch having successfully grinded against Dean’s prostate enough to light at least a small, flickering fire in Dean’s gut. His dick isn’t really into it, though, even if it tingles pleasantly when Dean squeezes himself.He considers actively imagining Cas for about half a second before he mentally berates himself. He hasn’t needed Cas like that before and he certainly doesn’t need him now, that’s a load of bullshit right there. Plus, it would be kind of creepy to consciously choose to do it while getting fucked by someone else, rather than what accidentally happened last time with Michael, right? Cas would be creeped out if he found out, right?As Dean is pressed down onto his stomach, dick pressed against the silk sheets, he considers the possibility that Cas will, in fact, be happy to hear Dean fantasize about him again. He’d certainly been pleased last time. Pleased enough to call and talk Dean into coming all over himself and now that he thinks about it, he needs to remember to fix the button on his shorts. The wind is knocked out of him when Ketch more or less mounts him like a fucking bull in heat. He shoves his hard dick into Dean’s ass all at once, making them both grunt, though perhaps for different reasons. Dean is happy Ketch has decided to fuck him from behind tonight because he feels less apt at schooling his expressions than normal. He grimaces when Ketch starts ramming into him almost immediately and when he bends over Dean’s back to bite his shoulder, Dean’s yelp of pain is the realest sound Ketch has ever managed to draw out of him.“So fucking good,” Ketch growls, his punishing grip on Dean’s slim hips sure to leave bruises, dick drilling mercilessly into Dean’s ass. “Tight.”“Yes, Daddy,” Dean moans, shoulder throbbing where Ketch gave him more than a little love-bite. He claws at the bed, thighs quaking when Ketch puts more weight on him. If there’s one thing that’s certain, it’s that Ketch thinks Dean can take it harder just because he’s a guy. The thought that maybe he has Dean as a sugar baby instead of a petite woman precisely because of that reason and maybe that’s why he seldom bothers to touch Dean’s dick enters Dean’s mind for the first time as he gets fucked into the mattress. The same mattress he has been pushed down into before, too many times to count, but fuck, it only strikes him now how likely that is. Well it’s not like Dean is going to ask but if it’s true it makes him feel pretty damn fucking stupid for all those times he did get hard and actually came from getting fucked by Ketch. It’s a pretty dumb fucking thing to be thinking about during sex but thankfully it’s over not much later. Ketch groans gutturally when he comes, biting down on that same goddamn shoulder, which makes Dean’s whole body clench up with pain. Unlike Michael, who at least usually does his best to at least afford Dean a reach around, Ketch simply rolls to the side, slapping Dean on his ass.“Great as always, doll face,” Ketch grins and Dean plasters on what he hopes is a demure smile. “You ready for round two or are you getting up in the morning?”Dean’s stomach turns at the thought of any more rounds, possibly ever. He sighs dramatically, rolling to his back and stretching.“I sadly have to get up.”Ketch nods. “Well you know where the shower is. Treat yourself.”“Thank you, Daddy,” Dean chirps, leaning in to kiss Ketch on the cheek before bouncing off the bed.Well, trying to look as if he’s bouncing. As if he got a really good dicking and feels invigorated, instead of feeling like his body has been pummeled and the lube smears unattractively between his ass cheeks.Thankfully Ketch, like all of Dean’s Daddies, is respectful when it comes to Dean’s wishes and his schedule so he doesn’t question or get mad about Dean leaving and not staying the night. Dean is even treated to some necking by the entrance, which he allows for a while, making fake happy noises about the attention. In the elevator ride down, he inspects his neck and makes a face at the marks. Unlike when he left Cas’ last time and kind of hoped to see some marks, he feels annoyed to see them now and he rubs his skin even though he knows it’ll make it worse.He waits for a cab outside Ketch’s apartment complex, content to let the night air chill his racing thoughts. It’s getting colder, though never as cold as back where he grew up in Kansas and Dean is thankful for it. He wouldn’t want to be remembered of the winter nights when he and Sammy had to huddle together to stay warm after dad forgot to pay the bill.The cab ride is short and blessedly silent and Dean lets his mind go quiet and blank. Back at his apartment he finds that Michael has had a package sent to him. When he opens it, he finds a black shirt in a sheer, almost see-through lace-like material. Putting it on and looking at himself in the mirror he can immediately see his nipples peeking through the shirt. He wonders for a moment if he should put something on underneath but laughs it off. Not that Dean doesn’t have an abundance of nice lingerie that he likes to wear for his Daddies, but that’s not what this shirt is about. He understands perfectly well that he’s supposed to come looking half-naked and it doesn’t really matter since Cas is the only Daddy Dean likes to dress in lingerie for. The only one truly deserving of it.Ketch doesn’t care, he only wants a hole, Michael cares too much and Dean has made him come in his pants more than once just grinding his lace-clad ass against his crotch. Crowley seems at times both disinterested and intrigued but that can be true of any interaction they have, clothes notwithstanding. Cas, on the other hand…Dean puts the shirt back in the nice package it came in and turns to walk into his bedroom. The cleaning lady has been here, has made everything nice and tidy, but she never looks in his drawers. He knows she doesn’t or he’s sure she would have had some choice questions to ask, or maybe she’d just quit altogether. Because in one drawer there is jewelry, always unmoved, waiting for Dean’s next touch. In another are an abundance of sex toys, ranging from the ones Dean actually likes and some that he has bought himself to some rather questionable ones that he hopes the Daddy that bought them has forgotten. And in another drawer, Dean’s favorite, are his panties and stockings and bodysuits. There’s lace and frill and mesh and satin and Dean sometimes kind of wants to take it all out and lie in a pile of it because it’s so pretty. It makes him feel pretty and he fucking loves that for himself. One thing to be called beautiful and another to feel it, he thinks as he picks up a lace bodysuit with crisscrossing strings in the back. It’s hell to put on but Dean loves the way he looks in it. Like a sexy motherfucker ready to be fucked good and well.Like only Daddy knows how.Dean sucks on his teeth, indecisive. He shouldn’t indulge those kinds of fantasies. Should resort to the regular three Ryans to help him through this heightened state of awareness and arousal. But fuck, he just doesn’t think they’ll do it for him tonight. Or maybe with the help of this bodysuit?He bites his lower lip as he walks into his bathroom to remove his clothes, putting them in the now empty hamper. He means to take a quick shower to wash off the night he’s had but he stops for a moment in front of the mirror to inspect his shoulder. He hisses when he presses down on the bite mark but it’s actually not too bad. Washing it will probably be enough, even though he’ll keep an eye on it and maybe tell Ketch next time to watch it with the bites.Dean looks away from his mirror image at the thought of another time with Ketch, as if he feels ashamed for even thinking about it. He doesn’t know why, and it doesn’t make any goddamn sense why he would feel like that, other than Cas putting ideas in his head. Fuck, he’s been doing this for a long time and he has never felt dirty or like he is betraying someone’s trust. And since Dean picks his own Daddies — at least he has picked these four — he knows he’s at least a little attracted to them, on some level. So that shouldn’t be an issue, right? It shouldn’t be hard for him to have sex with them like usual?But suddenly Crowley’s touch feels more indifferent than usual, Michael’s feels boring, and Ketch is downright disgusting. Dean’s mind feels jumbled with what that has to mean and he can’t help but think he’s overreacting. Just because Cas said one thing about being Dean’s number one Daddy, Dean’s body and mind has gone into overdrive thinking about it and that’s just stupid. He shouldn’t be throwing away years of networking and sacrifices for one man, who for all Dean knows isn’t even that serious.Because sure, Cas wants to be Dean’s number one Daddy but what does that mean? A sugar Daddy isn’t a boyfriend and is that even what Dean wants with Cas? Surely not. And sure, Cas always says he could pay for everything Dean wants but Dean doesn’t like to put all his eggs in one basket. Because what if Cas is lying and he won’t help pay like he proclaims? Dean needs the money for Sam.But then again, he thinks as he presses his fingers against the bite again, the pain grounding him, maybe if Cas did mean it as something more than a sugar Daddy, then maybe the money wouldn’t matter. Dean would still need it, sure, but maybe he could get it somewhere else?Maybe…He gets interrupted in his thoughts when the mirror starts fogging over. Only then does he realize that he has left the shower on for a long time while he was just standing there thinking. Shaking his head, he hops in and rinses off, fondling his dick for a moment but ultimately deciding against it.Out in the bedroom in his fluffiest sweats, he puts away the bodysuit again. He has a date with Cas tomorrow and he knows for a fact that if he asks for it, Daddy will take ultimate care of Dean’s body. Better to come a little horny then, since Daddy knows what the fuck he’s doing and the anticipation sometimes makes it even better.Maybe he’ll put on something extra nice instead? The best clothes he owns for riling Daddy Cas up specifically.Dean smiles to himself as he fixes a very unhealthy and super delicious snack. Yes, he’ll watch some reality TV to rest his spinning mind, get a good night’s sleep, and then in the morning he’ll doll himself up real nice. Make a special surprise for Cas because why the hell not? If Cas proclaims to want to be Dean’s number one sugar Daddy, then maybe Dean should show the man his worth, make him beg for Dean’s attention.Fuck yeah, that’s a nice image, Dean thinks as he watches Below Deck, snuggled up on the very same couch where he had phone sex with Cas just last night.

----- CHAPTER BREAK -----

The next morning Dean wakes in a good mood, feeling energetic and practically bouncing off his bed. He breezes through his morning routine and when he’s in the shower after his workout, he takes a moment to prep himself.He doesn’t know what the date with Cas will lead to but he can certainly hope and it’s always nice to come clean and slightly stretched. While he’s in there, fingering himself, he indulges and lets his mind wander to the three Ryan’s, letting them take care of his body. Not all the way, though, so that he ends up coming out of the shower all hot and bothered, dick at half-mast and a huge grin on his face.There’s a certain spring in his step as he puts on the cologne he knows Cas likes the best on him, even going so far as putting a drop of banana flavored lube in and around his hole, in case Cas takes the hint and actually fucks Dean as soon as he sees him.To make that happen, Dean digs deep in his closet after the perfect clothes, landing on his favorite corset vest. It has a black base with green satin and gold thread inlays and partnered with a pair of tight-fitting, black suit pants it accentuates Dean’s waist and butt to an almost ridiculously perfect degree. If Cas doesn’t know he needs to fuck Dean ASAP in this then Dean thinks they should just call it quits right now.“Yeah,” he mumbles to his reflection in the hallway, straightening and pulling on the corset. “Yeah, you deserve this.”Deserves to dress up and deserves to treat himself.On his way out he texts Charlie to confirm that they’re still on for tonight. She has a new board game she wants to introduce to the gaming corner in her café but wants to try it out first. Dean loves being her guinea pig and he grins to himself when he reads her happy affirmative.Just because he feels like cruising, he decides to take his car instead of a cab and he enjoys the stares of both the concierge and a random guy in the garage when Dean sashays past them. Fuck yeah, he looks good and he knows it.Cas is the CEO of an architecture firm that he has inherited from his father because Cas comes from old money, although he’s thankfully not snooty about it, at least not around Dean. His firm has been around since forever and from what Charlie could find out about it, Dean now knows they were around to help build most of Las Vegas back in the day and Dean also happens to know Crowley has hired them for projects before Dean met him. Cas of course knows Crowley is one of Dean’s Daddies, because Dean hasn’t been able to keep his trap shut around Cas, but he has never behaved any way except professional about that fact and Dean kind of fucking loves that.That is to say, it’s sexy that Cas knows what he’s doing. That he doesn’t mix business and pleasure. Yeah, that.At the firm, Dean swipes his access card at the entrance and winks at the security guard, who only grins and shakes his head. He of course lets Dean through, knowing full well that Dean doesn’t work there but that Mr. Novak has ordered the card made for Dean so that he can come and go as he pleases. No one at the firm questions Mr. Novak and Dean is man enough to admit he gets a kick out of knowing such a powerful man is his Daddy.He rides the elevator up to Cas’ floor alone and pretends it’s because he too is important. Too important for the peasants to crowd in his space. Dean isn’t haughty like that but it’s fun to pretend and hell, half his life is just make-believe anyway. Sam isn’t wrong about Dean playing all kinds of games, although in Dean’s mind his are a little different than that of a college junkie who dared lay a hand on his little brother. Well, Sam seems fine now anyway and Dean doesn’t really have the time to think about that right now.Not as he sweeps down the corridor on Daddy’s floor, a self-satisfied smirk curving his pretty lips, knowing full well that more than one person sees him striding past their open doors.At the end of the hallway is a nook where Cas’ assistant sits, like a guard dog. Like a stereotypical secretary out of all the movies. Dean smiles pleasantly when he meets Meg’s unimpressed stare and she looks him up and down, rolling her eyes.“Nuh-uh,” she says, shaking her head. “He has a conference call at 11:30.”“Good thing I’m early, then,” Dean smirks, sliding past her.“You’re 45 minutes too early!” she snaps but he of course ignores her.He knows full well that he and Cas have a lunch date and that Cas has lunch at noon but it’s not like a pesky thing like time has stopped Dean before.Instead he just barges right into Cas’ office, walking in with the air of someone who owns the place, feeling confident enough to do so only with Cas. None of his other Daddies would allow this kind of behavior and to be frank, Dean is never this bratty with any of them. He’s never himself at all, if he’s being honest.But with Cas, he totally can be, and if Dean didn’t think so before then the look Cas gives him when his eyes land on Dean is enough evidence. Of course there’s an initial surprise there but fucking hell, it fades away so fast to yield to primal hunger that Dean feels Cas’ gaze lick his body like fire.“I’m a little early, Daddy,” he drawls, a certain twang to his voice. A greedy, needy twang that Cas always responds favorably to and that Dean doesn’t even have to fake. “I hope you don’t mind?”The door falls shut behind him just as he saunters up to Cas’ desk. Cas rises slowly to his feet, like a hulking beast, reaching for his intercom without looking away from Dean. He misses and presses a button that makes the intercom screech for a second and then gets it right.“Clear all my calls, Ms. Masters.”Dean’s lips stretch into a pleased grin and Cas’ eyes darken. Desire pumps through Dean, arousal going off as if Cas was actually touching him and yet all they’re doing is standing there, staring at each other over Cas desk.The intercom squawks and then Meg’s voice can be heard, a certain tired note to her tone.“I already did, duh.”That certainly makes Cas look down at the intercom and Dean has to suppress a laugh. Poor Meg, she usually has to deal with the fallout of Dean’s antics. Dean sure hopes Cas pays her well for her great efforts.The intercom squawks again before Cas can say anything.“Mr. Novak,” she adds, only a little bashfully.Dean can’t take it anymore, he chuckles to himself and rounds the desk, going to Cas just as he presses the button again.“Very well, Ms. Masters.”“Don’t be too hard on her, Daddy,” Dean says, pouting attractively as he puts his arms around Cas’ neck. “It’s my fault. I just couldn’t wait no more.”Cas immediately puts his hands on Dean’s waist, squeezing and pulling him as close as physically possible.“Tell me everything,” he growls and Dean for real can’t wait any longer, needs to kiss his Daddy right the fuck now and as soon as he does, he feels as if everything else melts away.Daddy has his strong arms around Dean, supporting him, and he easily takes over the kiss, dominating it and pushing into Dean’s mouth to taste all of him. Dean’s body is already hot, the little self-loving he indulged in during his shower coming back to force his arousal to the forefront of his mind. He undulates against Daddy’s solid frame, loving how dainty he feels when they hug like this.“God, I missed you,” Daddy admits on a shaky exhale, forehead against Dean’s. “You’re absolutely ravishing, sweetness.”“Then do it,” Dean moans, grinding his hips slowly against Daddy’s, showing how much he really needs it. Pleasure tingles out of his heated crotch, his hardening dick already begging for more. “Ravish me like no one else can.”Daddy chuckles and Dean feels his own heart thump faster at the sound. “Is that what this is about?” leaning in, he rumbles right the fuck in Dean’s ear. “Are your other Daddies not satisfying you anymore?”Dean whines, hiding in the crook of Daddy’s neck. He knew he shouldn’t have called Cas about that miserable sex with Michael and now here he is, again admitting that he needs more than what he’s getting but fuck if he can think rationally right now. He wants this, wants Cas and needs to not have to think for a while.“I hear you, sugar pie,” Daddy rumbles sweetly, using his sure grip on Dean’s body to twirl him around so that he can press against Dean’s back and ass instead, still talking against his ear. “I can’t say I haven’t been yearning myself.”His hands drag up and down Dean’s body, digging in at all the right places and making Dean buck back against him. Fuck, Daddy is already hard in his nice dress slacks and Dean grinds greedily, hole clenching needily. He tries to stifle a moan, he really does, but it’s fucking difficult when Daddy touches him in all the right ways. He pants, eyes unseeing as he leans his hands against the desk, body shuddering when Daddy kisses his neck, big hands massaging Dean’s slim hips.“Tell me what they did wrong,” he asks, voice deliciously deep and dark with his arousal. “Tell me how to do better.”He’d asked this last time too, hadn’t he? Dean’s whole body pulsates with raw desire, overwhelmed with how well Daddy takes care of him.“He was too rough,” Dean whimpers out. “I didn’t get to come.”“Didn’t get to because of ejaculation play?”Fuck, Daddy just ups and cups Dean’s straining dick right then and it makes Dean thrust forward so hard his thighs hit the desk. There’s a glass of clear liquid on the desk and it threatens to spill over what might be important documents but it thankfully doesn’t. Not that Dean fucking notices.“No,” Dean shakes his head, looking over his shoulder with glossy eyes. “Because it was so bad.”Daddy looks like he kind of wants to laugh at that. No doubt at the expense of the man who was so unsuccessful in pleasuring Dean. But he doesn’t and Dean will later give Cas credit for that. Right now he’s too occupied with feeling needy and looking desperately at his Daddy.“Oh sweetness,” Daddy sighs and leans in to kiss Dean on the cheek, regretfully letting go of Dean’s poor dick. “I thought you liked it a little rough?”Dean moans, rubbing his whole body back against Daddy’s. “I like it with you,” he stupidly admits. “You do it without being too rough.” Dean’s shoulder is still smarting, although there is no visible bruising, thank fuck. “And you do aftercare…”Daddy exhales what sounds like a strangled growl and every hair on Dean’s fucking body stand on end. He holds his breath, feeling as if he’ll fucking explode in his pants if he so much as moves, too overcome by Daddy’s protective possessiveness.“Don’t worry, sugar pie,” Daddy rumbles, pushing some things on the desk to the side so that he can encourage Dean to lean down on it. “Daddy will take care of you.”With that, he detaches from Dean’s back to get his chair, sitting down behind Dean just as he reaches for Dean’s crotch to start opening his pants.Dean’s breathing hitches and he stares wildly behind himself. “Are you gonna eat me out, Daddy?” his pulse skyrockets when Daddy gropes his ass for a moment. “In your office?”“My little sweetness needs taking care of,” Daddy states, pulling down Dean’s pants just enough to expose his butt so that he can kiss one of the cheeks, speaking the next words into the heated skin there. “Daddy is here for you.”Oh fucking hell, this is glorious. This is better than what Dean had anticipated and he has to put a hand over his mouth to stifle the moan that claws up from deep within his chest. Pleasure pulsates like liquid fire through his veins and he feels himself shaking as Daddy kisses and massages his ass for a moment, encouraging Dean to relax against the desk, as if relaxing is even possible for Dean right now.His dick throbs and his legs threaten to give out when Daddy spreads his cheeks. Of course Daddy has him and rolls right the fuck up with his chair, putting his feet against Dean’s so that he can support him should he actually fall. Dean does his best to keep it together at least a little bit and manages to lean his chest down against the desk so that his ass is in the air, right in Daddy’s fucking face and shit, Dean has been eaten out a lot of times, especially by Cas, but this is by far most hot and bothered he has become. And they haven’t even fucking started yet.“You smell sweet,” Daddy murmurs, his mouth so close to Dean’s hole that his warm breath ghosts over the sensitive skin. “Did you prep yourself for me?”“Yes,” Dean moans, feeling his dick twitch when Daddy momentarily squeezes him harder. “I didn’t know if we’d do anything but I wanted to be prepared.”“You came in here in this,” Daddy taps Dean’s side to indicate his corset. “And you were still unsure if I’d fuck you or not?” he hums disapprovingly and Dean thinks he feels Daddy shake his head. “That’s on me. I’m sorry, sweetness.”Dean doesn’t really know what Daddy is talking about, his mind is too filled with arousal and desperate need for him to comprehend things larger than Daddy’s hands and mouth on him. Turns out, he doesn’t have to process much of anything, because in the next moment, Daddy has pressed his whole damn face against Dean’s ass and fuck, that’s his tongue.It's long and clever, knows all of Dean’s creases and spots and fuck, when Daddy spears it like that, it reaches so far into Dean. His breathing stutters and he tries to spread his legs further. His pants are of course in the way and the restriction makes him whine needily. Pleasure shoots through him and he can feel his balls pull tight for a moment.Daddy groans, the vibrations spreading inside Dean’s body, and licks deeper. The banana flavored lube seems to do the trick for him and he eagerly laps it up, getting Dean’s ass wet and hot in no time. Dean loves that, loves feeling so desired, but the best part is for sure when Daddy fucks Dean on his tongue. It’s hot and soft, reaching past his rim and into parts of Dean that yearns for the older man.Daddy keeps making these little eager, encouraging sounds as he eats Dean out that hype up Dean’s arousal, making him desperate to take his dick in hand and stroke himself to orgasm. But what a fucking waste that would be, he knows, loving feeling at Daddy’s mercy just knowing the reward will be so much more satisfying when Daddy delivers it.“You’re so precious,” Daddy groans, pulling away to nip at Dean’s ass. Not hard enough that it hurts, not that Dean would mind this time round.Actually, having indents of Daddy’s perfect teeth would feel pretty fucking good, Dean thinks hazily, and he can’t help but grind back against Daddy’s face.“Eager, sugar pie?” Daddy chuckles and fuck, maybe Dean will come like this? Untouched and all over Daddy’s desk.He whines, pressing his legs together at the sudden urge, the absolute fucking need to come right the fuck now. He lets out a short gasp, reaching down to grab the base of his dick. Fuck that was close, and now here he is standing as if he has to pee and fearing that even something as small as breathing will make him go off.Daddy, meanwhile, has either not noticed the impact he has had on Dean’s body or he doesn’t actually care about his office furniture. Fuck it would be so hot, though, to mark all of Daddy’s belongings. To have the man be Dean’s and—“Shit,” he gasps when he feels that pull so soon again. “Daddy, I—”“I hear you, sweetness,” Daddy murmurs sweetly and Dean has to wonder if Daddy has watched him squirm and enjoyed it but fuck, he can’t think too much about that right now or he might actually come.He can feel it gathering, deep inside him, and just as Daddy reaches over to one of his desk drawers, Dean feels a dollop of precome drippling out. And it feels so good. He smears it over the swollen head, down under to the glands there, and his whole body throbs in tandem with his pleasure.“C’mere,” Daddy mumbles and actually turns Dean a little so that he can show him a condom he has somehow magically produced.“You gonna fuck me, Daddy?” Dean breathes, desire choking him.Daddy tuts, smiling and opening the condom wrapper. “You know I love to make you scream. Can’t scream here, sugar pie.”But the motherfucker rolls on the condom without as much as a heads up, as if he wants to test Dean’s ability to obey even unspoken commands. Dean has to slap a hand over his mouth, body jerking, his corset suffocating him as he feels his orgasm teeter right there.It takes him a moment to calm down and when he does, he realizes he’s half-way sitting in Daddy’s lap, Daddy’s big hands on Dean’s back and inner thigh.“Daddy,” Dean whines, shaking.“Up you go, sweetness,” Daddy rumbles, sounding strangled himself. He helps Dean to lie face down on the desk again, ass presented and that’s when Dean sees the second condom.“I think I’m good with one,” he mumbles even though it feels as if he’ll come so hard the fucking rubber might come shooting off and land on the floor.But really, what’s up with the second condom if Daddy isn’t going to fuck him right now?“This is for me,” Daddy grunts, wrestling his absolutely fucking massive cock out of his pants. Dean’s eyes bulge out. Daddy’s cock is always perfect but he just hadn’t thought Daddy was that affected. “I wanted to focus only on you,” he chuckles again and Dean sees Daddy’s cock straining when he rolls on the condom. “But I just can’t control myself today.”Oh fuck. Dean feels it, like a relentless force, and it feels so fucking good, the pleasure so sharp and palpable that his vision is swimming. Daddy wants him so much he thinks he will come in his pants if they continue. Daddy wants him.Dean jumps when he feels Daddy’s tongue back on his twitching little hole and he melts down against the desk, letting the emotions and pleasure wash over him. It’s heated now, Daddy eating him out greedily, as if he’s really preparing Dean for a good fucking but it’s okay that that’s not the end-goal this time. Dean can feel the desire in the way Daddy licks and sucks, how he fucks Dean on his tongue, and how he massages and gropes Dean’s ass cheeks.Daddy is greedy and possessive and right there, in the V of his open slacks, is the physical proof of his own yearning, of how much Dean affects him. If Dean was to stumble back just the slightest, he could sit right down on Daddy’s cock and suddenly it’s all he wants. Wants to be spread open on Daddy, squirm in his lap, feel Daddy fill him up when Daddy can’t hold it in anymore, because Dean is so fucking sexy even someone as calm and collected as Daddy loses control.Fuck, the edge.“It—”Dean doesn’t manage to say anything more because it’s coming, shooting out of him as he tumbles head-first over that fucking edge. He shakes, gasps, knees giving out as he fills the condom with spurt after spurt, leaving him a babbling mess.“Dean,” Daddy—Cas—grunts then, pulling on Dean so that he turns.Dean stumbles, unsteady on his feet, but he smiles when he sees how close Cas is to coming.“That,” he says huskily, putting a knee on Cas’ chair, right between his spread legs, awfully close to his throbbing cock. “Was fucking amazing.”He leans down, cupping Cas’ face as he kisses him, chasing the taste of himself and the banana lube right as Cas grabs him, grinding his cock against Dean’s knee and thigh for just the slightest moment. And then he’s coming too, groaning into the kiss, and Dean feels fucking euphoric.He made that happen. He made Daddy—made Cas—come like this. It’s such a fucking rush and Dean doesn’t even know who messed up who more in the end.“And just in time for lunch too,” he says cheekily when Cas looks like he has gathered himself enough.“You’re a menace,” Cas says, way too affectionately. “But it sure worked up an appetite.”“Weird,” Dean smirks, going to Cas’ private bathroom. “With how much you just ate you ought to be full.”“Absolute menace,” he hears from outside the bathroom and his smirk widens to a grin as he wipes himself clean, righting his clothes.They end up going to a hole-in-the-wall burger joint that’s far less classy than anything Dean’s other Daddies take him to but that he fucking loves, and Cas listens to Dean babble about the game he and Charlie are playing tonight, smiling all the while.After lunch they kiss goodbye outside Cas’ firm, and Dean sails home on fucking cloud nine. He spends the afternoon driving Sam to some museum or other that he claims is for school but that feels decidedly date-like considering he has Jess with him, a really nice girl Sam has mentioned a few times before and that Dean understands doesn’t study criminal justice law and hardly would have the same assignments as Sam. He doesn’t say anything about that, though, just happy that Sam hasn’t mentioned Ruby in a while now and by the time he gets to Charlie’s, he’s in a really good mood.She makes the mistake of asking him about it, and since he apparently has no brain-to-mouth filter about this, he ends up gushing about Cas.“I think he would like this game too,” he says, unaware of how much he’s talking, smiling like a dork as he helps with unpacking all the bazillion pieces. “He’s very meticulous and I know he has the brains for something like this.”It’s a strategy game called Hallow’s Fall and it seems big and complicated. Charlie is on the fence whether it’s complicated in a cool way or just convoluted, hence why they’re testing it out before she brings it to her café.“Is that so?” she asks, clearly amused. Not that Dean notices.“Yeah like, there’s some diplomacy aspects to this, right?”“I think so. I mean, it—”“Cas would ace that,” Dean interrupts, smug as if he has just proven a great point. “He’s such a smooth talker, he could talk a telemarketer into buying things from him.”“Dean,” Charlie says, clearly holding in laughter. “Do you wanna call Cas over?”That stumps Dean because yes, how fucking awesome wouldn’t that be?!But also no, what the hell?“No,” he says, much less vehemently than it sounded in his mind. “Why, uh, would I, um…?”“Because you’ve been here almost an hour and you haven’t stopped talking about him,” Charlie exclaims, clearly unable to hold in her laughter as she giggles at his no doubt stupid face. “Seriously, he’s it for you.”“Nuh-uh,” Dean mumbles uselessly, sagging in his seat. He stares down at the game pieces, thinking over his own words. “I just like him, because like, he’s the easiest to work with, so…”Charlie nods but it doesn’t feel like she’s agreeing with him. “Then why don’t you work with him exclusively?”Dean bristles but deflates immediately, looking at his friend as Charlie sorts what seems like a redundant amount of different coin tokens.“You know I need the money,” he says lowly. “For Sammy and stuff.”Charlie shrugs. “I’m sure Cas can pay for all of that, if he’s as rich as you say he is.” She looks up, the smallest of concerned wrinkles between her eyebrows. “Unless you think he’s scamming you?”“No,” Dean says without hesitation. The thought has never crossed his mind that any of his current Daddies wouldn’t be who they say they are. Dean has a very thorough vetting process in place. Although to be fair, he did move awfully quick when it came to Cas… “No, I just mean that college is expensive and stuff.”“Dean,” Charlie scoffs and goes back to counting tokens. “Regular families can afford to pay for college. I think a freaking CEO would have no problem.”That’s probably true and to be honest, Dean doesn’t really need his fancy apartment or the clothes, and he likes the simpler food better anyway. So like, if Cas couldn’t afford all of that, Dean could give that up for something cheaper. His main focus is getting Sam through college anyway.But is that the kind of relationship Dean really wants with Cas? If Dean was to end his partnership with all of his other Daddies and just keep the one, wouldn’t that change the dynamic? Dean would become more dependent on Cas for sure and is that what he wants? No, with Cas he would want more, and that’s what’s freaking him out.“I can’t want that with him,” he mumbles. “It’s scary to think about.”“Why is that?” Charlie is frowning at the coin tokens, looking as if she’s missing some. “You do everything for your little brother, and you’ve told me you even took care of your dad when he got sick and everything.” She looks at him with soft eyes, putting a hand on his arm. “When is it time for Dean, huh?”Dean swallows over an unexpected lump. “What if he doesn’t want me like that, though?” he shrugs when she looks at him as if he’s stupid for thinking so. “I don’t have anything but my body to offer.”“Okay,” she says, tone all business-like. “But from what you tell me, you and Cas at least have something in common. He’s kind of nerdy too, isn’t he? You have things to talk about.”“That’s true,” Dean mumbles, smiling slightly when she looks smug. “He’s the only one I don’t have to put on a façade with all the time.” He frowns for a second. “Him and Crowley, come to think of it.”“You’ve never talked about Crowley.”To be fair, Dean hasn’t really spoken about any of his other Daddies with Charlie. She knows he’s a professional sugar baby and she knows he keeps multiple Daddies, but that’s only because she was there to witness Dean in action that time when Cas happened upon her internet café.He waves his hand dismissively, not really one to divulge too many details. It would be highly unprofessional to go around and telling everyone and their aunt about the guys Dean lets fuck him for payment and trinkets, after all.“He’s just one of them, but he’s nice. Treats me like more than a pretty thing.”“So, kinda like Cas?”Dean opens his mouth but closes it again, unsure of his words. Because yes and no. In a lot of ways Crowley treats Dean exactly like Cas, listening to what he has to say and asking his opinion on things. But in a lot of ways they’re almost painfully different. Like how Cas is also affectionate and soft with Dean, and how he fucks Dean within an inch of his life, making Dean cream every time.Crowley, on the other hand, is mostly strictly business-like and it has been months since the last time the older man fucked him. Sometimes he has Dean suck him off, but that’s become less frequent as well.Dean leans back in his chair, sighing. “I just don’t need this thing with Cas to become something bigger than it is, y’know?”Charlie looks like she kind of doesn’t know and Dean doesn’t blame her. He bets she has never really been in his situation, doubts a lot of people have.“Why don’t you just take one day at a time, then? See how it goes?”“See how what goes?” Dean asks suspiciously, squinting at her when she grins and gets up to get a bottle and two shot glasses.“This thing with Cas that’s totally not a thing,” she elaborates, putting the glasses on the table and pouring a generous amount of what looks like vodka in them. “Listen, all I know is that I’ve known you for a few years now and you’ve never talked about another man like you talk about Cas.”It doesn’t sit right with Dean, how obvious he suddenly is about this. How bad he is about hiding his feelings. Him, who depends so much on his acting skills. It’s all Cas’ fault, he thinks sourly. Just because he happened to mention wanting something with Dean, wanting to have more. That apparently opened something deep within Dean, a kind of vacuum that only Cas can fill, and Dean doesn’t really know what to do about that.“Can we stop talking about this?” he grouses. “Let’s just play the game already.”“Sure,” Charlie says brightly and gestures to the glass in front of him. “Take a shot.”Dean raises his eyebrows. “Is that part of the game?”“No,” she giggles, downing hers in one swig. “But you need it.”Bless her, he fucking does.

----- CHAPTER BREAK -----

“No, bring the lavender one again.”The saleswoman bows gracefully at Crowley’s dismissive tone and goes to fetch the shirt Dean just had on.“Picky, are we?” he teases.He’s standing on a little platform in front of four mirrors, in the suit Crowley has had tailored for him. It’s in charcoal gray, snug around his waist, and with a matching vest. Crowley had insisted on coming on this last fitting, to pick out the dress shirt he wanted Dean to wear with the suit.The store is of the fancier kind, the one where they serve champagne with the fittings and most of the interior is in mahogany with gold paint. There are a lot of clients but the saleswoman doesn’t seem perturbed at being stuck helping Dean, probably because Crowley is a regular and she knows she’ll be paid handsomely in commission.“It’s an important meeting,” Crowley says, not even looking at Dean but instead down at his phone. “I need you to look your absolute best, crumpet.”Dean smiles to himself, undressing. He doesn’t know why Crowley wants Dean to sit in on this meeting,  but he is kind of excited. It’s for the housing he’s building in Rosewood, the one he was in the news about, and Dean thinks they sound like a good idea. Affordable houses built near low-income areas? Sounds like something Dean could have used when dad got sick.He smiles at the woman when she hands him the lavender shirt, quick to put it on. She helps him straighten the vest before putting on the suit jacket too, even though he doesn’t need the help. She does a good job of folding the pocket square and Dean is pleased to see she has picked one that matches his shirt. She doesn’t afford him a smile, too professional for something like that, but she does pat him on his chest as if she thinks this looks good.“What do you think?” Dean only barely refrains from adding “Daddy” on the end there. Crowley isn’t big on Dean using that moniker, even less so now than when he and Dean first met, and Dean knows Crowley likes that Dean remembers.Just to be a little shit, Dean has taken to calling Crowley by his first name instead, something only a few are allowed to do, and to his delight, Crowley allows it, sometimes even with a smile.Crowley looks up at Dean’s question, getting off of the plump armchair he has been sitting in, and comes up to Dean, touching the suit in various places. As if he’s testing the seams or something. Dean smiles down at him, holding his arms out in a little tada-motion.Crowley nods, patting Dean on his waist. “This’ll do.”Great praise coming from him, Dean knows. The saleswoman doesn’t even look nervous so supposedly she knows that as well.They walk out of the store with Dean’s other clothes in a bag, suit on and paid for in full by Crowley, of course. Just like all of Dean’s Daddies, Crowley has a limo that chauffeurs him around, but he also has a regular car that he enjoys driving, like Cas.Dean grits his teeth at the thought of Cas. He keeps invading Dean’s mind at the most inopportune moments and Dean really needs it to stop or he’ll have to start facing the music. But it can’t be as easy as Charlie seems to think it is, good things don’t just happen to Dean, not without some kind of compensation.So he staunchly ignores all thoughts of Cas and jumps into the Aston Martin Crowley imported from England just because he wanted to. Because he can. Because he’s the kind of haughty rich person that does whatever he likes. And yet, Dean thinks as he watches Crowley drive, here he is, building houses for the poor.“What?” Crowley asks after a while and Dean sucks on his teeth for a moment before deciding to be honest. Crowley has always liked that the best anyway.“I’m proud of you.”Okay, that surprises him just as much as Crowley.“Elaborate, love,” Crowley demands after a stunned silence.Dean looks away, studying the scene out the windshield without really seeing what zips past the car.“I dunno. I guess I’m happy you’re doing this housing project.”“You think it’s not like me to help people?” Crowley is smirking when Dean glances at him. “Even after everything I have done for you?”Dean squirms, feeling the suit like a straitjacket around him for a second. “I didn’t mean anything bad…”“You’re not wrong,” Crowley says then, patting Dean on his knee. “I get funded by the city to do this. It’s free publicity.”There’s a glint in his eye when he says that and Dean actually relaxes. That’s the Crowley he knows, profiting in every scenario.“Well, still,” he says, smiling. Because really, what does it matter if it’s a publicity stunt as long as people can get good homes? “It's for a good cause. Some people live their whole lives dreaming of owning or even renting a house.”“You would know, hm little bird?”A thought strikes Dean and he squints at Crowley. “Is that why you want me at this meeting? As a cautionary tale?”That makes Crowley chuckle and he shakes his head, stopping for a red light. “Cautionary tale for what? You made it out and you did so brilliantly. No,” he pats Dean’s knee again, leaving his hand there as he starts driving again. “I want you there because you have lived those lives, you know what a struggling family needs the most.”Dean feels dumbfounded.  “Uh, you want me there as an advisor?”“I do,” Crowley nods to himself, his hand a comfortable weight on Dean’s knee. “What the hell do I know about living poorly? Aside from relating to absentee parents, I had everything I needed, and so did the old coots in these planning committees too.”“That’s…Fergus…” Dean doesn’t know what to say. Sure, Crowley has brought Dean with him to a lot of meetings before, but he has always just been made to sit in the background, like an ornamental bird to show Crowley’s obvious status and power. Crowley has asked his opinion afterwards sometimes, sure, but Dean has never been asked to speak at a meeting. “Thank you.”“It’s nothing special,” Crowley grunts, removing his hand. “Just give your opinion when asked, don’t speak out of turn.”So not like a complete equal but still more than a pet or set piece. Dean will take it and he’ll treasure this sudden power dearly. Fuck yeah, with this he can actually make a difference for people in need, or at least attempt at helping. It’s more than Dean has ever thought he would be able to and he can’t help but grin to himself the rest of the way, completely missing how Crowley smiles at him.At the meeting, Crowley introduces him as if he's some kind of resident expert on The Poors, as if he has been studying them like that gorilla lady, but Dean doesn’t complain. He just smiles politely and answers gracefully and with much insight whenever he is asked a question. Mostly they’re about arbitrary things like what would be most valuable to a family of lower income, a lawn or garage, and Dean does feel he has more to add but he bites his tongue, mindful of Crowley’s command.Because even though this feels like more, feels like something real and important, Dean knows very well that he is first and foremost Crowley’s sugar baby and a good boy obeys his Daddy.It kind of irks him at some parts but when he and Crowley leave the meeting, he knows he did the right thing keeping his pie hole shut. Crowley positively exudes satisfaction and Dean grins widely when they’re alone in the car again.“Did I do good, Fergus?”Crowley reaches over and puts a hand on the back of Dean’s neck in a way that’s reminiscent of how he does when Dean sucks him off, or used to do. Dean’s body tingles at the memory, drawn to Crowley at this moment.“Very well, crumpet,” he murmurs, eyes on the road but thumb stroking Dean’s neck.“Good enough for a reward?” Dean asks huskily and to his delight Crowley smirks.“I would say so,” he answers in an equally enticing tone and Dean feels a thrill go through him.Fuck yeah, Dean wants it right now. Crowley isn’t as good as Cas but he’s good enough and Dean is actually feeling pretty excited now, high on his success at the meeting.Crowley takes them to the privacy of his own home, which Dean isn’t against. He’s comfortable in Crowley’s space and has been there enough times to feel safe. Inside the door he hangs his suit jacket on the hanger by the door, complete with coat-hangers and all. He’s careful with doing it right, wanting to show Crowley that he cares about the suit, which he does, and then he turns to the older man, completely ready to do stuff. Might even kiss, something Crowley doesn’t do a lot.But Crowley isn’t behind him. In fact, he’s walking away, towards his home office.“There’s brandy,” he says, gesturing to the couch and the nearby liquor cabinet.Dean of course knows there’s brandy in there, he has poured enough drinks for Crowley, and that’s what he assumes is expected of him now too. Not that Dean needs booze to have sex with any of his Daddies, but sure, he could go for a sip.With that in mind, he pours more generously in Crowley’s glass than his own, since it felt like Crowley wanted a drink more than him. Maybe he’s nervous, Dean thinks with a smirk as he sits down on the plush couch. It has been a while since they had sex, after all, and Dean doesn’t think Crowley keeps any other sugar babies, or lovers.He frowns in thought. Come to think of it, when was the last time they had sex? That charity gala thing around Valentines? But that’s like six months ago. Has it really been that long? Damn, Dean feels like he’s been neglecting his sugar baby duties here… Then again, Crowley hasn’t exactly been asking for it either, so maybe he’s just not interested?Dean’s frown deepens and he puts his brandy glass on the coffee table, suddenly feeling worried. Because if Crowley doesn’t want him for sex, then what is he good for? Is Crowley dropping him?“Here we go,” Crowley says as he comes back into the room, holding up a square box and smiling, a rare sight. “This is for you.”He sits down beside Dean and hands him the box. A surge goes through Dean but no, it’s too big to be an engagement ring, thank fuck. Dean likes Crowley a whole lot but marriage material he is not, at least not for Dean. It does look like it came from a jewelry store, though, and when Dean turns the box to read the label it indeed says “Harrods”.“Fergus,” he mumbles, opening the box to find a clearly expensive wristwatch inside. It looks to be made in stainless steel, with a circular dial with a dark face and arms in gold. “This is…”Crowley nods, looking pleased when Dean removes the watch to try it on. “It’s my reward to you, for making a good impression at the meeting today.”This? Dean looks from Crowley to the watch. This is his reward? Not sex?Dean feels around inside himself, trying to gauge if he’s disappointed or not. On a small level, yes because he’s kind of horny and Crowley is a good lay. Not as good as Cas but certainly better than his other two Daddies.But on the other, much bigger, hand, this feels different in a good way. This feels like Crowley actually appreciates him as a person and not just a sex object. Although to be fair, buying pretty things for their sugar baby is a pretty standard practice for any Daddy. But then Crowley had mentioned the meeting again and Dean starts to feel pretty fucking great about himself.“Really?” he says and easily slips the watch on, satisfied that it fits. It looks good on his wrist, especially paired with the shirt and his suit. He looks classy, elitist, and he likes the feeling.“Indeed,” Crowley says and leans back on the couch, smiling at Dean. “A real man checks the time on a proper watch, Dean. Not just his phone.”“And I’m a real man?” Dean asks teasingly, preening as he looks closely at his watch. The face of it seems to glitter when he moves his wrist, not much but enough to make it appear shiny.“You are,” Crowley concludes easily. “You just haven’t found your footing yet. A nice exterior can help with that,” he smirks when Dean looks at him, surprised. “That and a successfully executed meeting with other hotshots. Don’t you think so?”Somehow, in that moment, Dean feels something passing between them. Something deeper, more real, than the exchange between a sugar baby and their Daddy. Crowley is looking differently at Dean, expectant and encouraging, and Dean feels himself soaking it up like a fucking sponge.“Yeah,” he says, smiling and bringing his brandy glass up in a toast, deciding on a whim to take a chance. “Here’s to many more.”A thrill goes through Dean when Crowley raises his own glass in response. “Hear, hear,” he mumbles, a satisfied smirk pulling on his lips. ***** Several hours later Dean is still reeling. Because if he is not mistaken, Crowley is offering more than just a sugar baby/Daddy relationship. And not more in the sense of a romantic relationship. Dean isn’t completely clear on what it is Crowley wants since he hadn’t dared push for more back there on Crowley’s couch, partially because he had felt overwhelmed already and partially because Crowley hadn’t initiated a discussion about it either. But it’s clear that he aims to treat Dean more as an equal, if the conversation that followed was any indication. And if Dean is being completely honest, things have felt different with Crowley for a long while, or maybe always.Not different like how it feels with Cas, but good too, better than with Ketch and Michael. Like he doesn’t have to play so many games with Crowley, which is probably why the sex has stopped, or tapered off. Coming out of his bathroom, Dean eyes his drawer of lingerie, feeling his body thrum with something. He had been fully prepared to have sex with Crowley there, and not just because he thought it was something his Daddy would want, and his body is feeling a little left out. His mind was satisfied and on a whole Dean is very happy with how the evening went but damn, maybe he needs something more right now?Biting his lower lip he lets one hand drag down his front, cupping his dick. Yeah, definitely interested. Maybe he’ll put on something cute and let the three Ryans take care of him? That sounds very nice, to be honest, and Dean is walking over to the drawer before he can change his mind.In it he finds a bodice in black lace, the one that makes him feel extra raunchy because why the fuck not? Dean likes admitting that he’s a proper cockslut, at least to himself, and putting on this bodice always feels nice. It hugs his body in a very flattering way, a patch of satin covering his growing dick and balls, snug and smooth. The lace is of the good quality that doesn’t scratch but it still feels deliciously tender where it rubs against his nipples.Fuck yeah Dean loves playing with his nipples. Walking over to a big body mirror in his bedroom, he pinches his nipples, hurrying on the process, and it makes pleasure blossom inside him, spreading pleasantly as his nipples pebble up. He sucks in a breath, almost hissing, and squirms in front of the mirror, looking at himself with hooded eyes. He’s not vain enough to get excited by his own visage but rather it’s how he thinks his partner will react to seeing him like this.The Ryans always love it, always love to smooth their hands all over Dean’s body to feel his heated skin under the lacy bodice. They have big hands, bigger than Dean’s, so he closes his eyes as he stands there, caressing himself. All the way from his hips, over his stomach, stopping at his sensitive nipples, up over his neck, squeezing just right, a pull on his hair, and then back down again to press against his dick. It’s so hard now, trying desperately to tent the tight bodice. No dice, though, and Dean has to adjust himself so that his dick is resting up against his hip. Fuck, that pressure is just right. His whole body is tingling with pleasure, heat thrumming inside him, and fuck maybe he should lie down?The Ryans think that’s an excellent idea so Dean goes to lie on his back on his bed, grabbing the sheets as he thrusts lazily up so that his dick presses against the bodice. The Ryans are all around him, touching him, praising him, kissing him. Fuck yeah, Dean loves getting kissed, all over. And he loves to reciprocate.Bringing one hand up, he sucks on two fingers, eager to have something in his mouth. That would be hot, he thinks, to be made to suck someone off while he’s dressed like this. Daddy always loves to see him in lingerie but he doesn’t think he has shown him this one yet. Wonder if Daddy would like it?Dean moans at the thought, hips rolling with jerky motions now. He squeezes his thighs together for a moment, the pressure feeling so fucking good. Pleasure throbs out from his groin and he starts moving in tandem, sucking on his own fingers and pinching his nipple again. In his mind’s eye, Daddy is over him now, on all fours, just out of reach because Daddy’s a fucking tease like that sometimes. He’s smiling his handsome smile, talking filth like only Daddy can. Stuff like “you look so good with something in your mouth, sweetness” and “Daddy can’t wait to fill your tight little hole”. Dean moans loudly, unabashedly, fighting the urge to roll over and rut against the bed. Because that would mean losing Daddy and Dean just can’t right now. He wants the man so badly that his desires leave him aching and he wants it like this, so that Daddy can kiss him.“Yeah you like Daddy’s kisses, don’t you?”Dean fucking loves them. “You want Daddy to kiss you somewhere special, right?”Like what happened in Daddy’s office? Fuck yeah, that was so fucking hot. Daddy had been so hard for Dean, wanting Dean so much he lost all control and Dean still rides the high of that, even now when he’s alone and all he has to keep him company are choice memories.“You drive me crazy,” imaginary Daddy says and Dean’s breath hiccups. “Yes, yes,” he gasps, wanting Daddy to go all feral on him.Dean’s body rolls faster and faster, the bodice dragging over his dick, holding it down and providing friction that makes him choke on his pleasure. It’s building inside him, the heat traveling through his body faster and faster, his desires for Daddy coiling inside him, tight, tight, until he can’t take it anymore and he has to put a hand on his dick.“No,” Daddy growls and Dean mewls, coming untouched into the bodice.He groans, body locking up, dick pumping and his hole clenching with every pump, desperate to milk something—someone.“Fuck,” he moans and then again, when everything catches up to him, “Fuck.”Because what in the actual hell is he doing? He started this because he was a little sexually frustrated since Crowley hadn’t fucked him. That evolved into his favorite masturbation fantasy, aka the one where three handsome actors take care of him.And then fucking Cas had showed up like what the fuck?“I need to get my shit together,” he mutters to himself, rolling off the bed and peeling off the now soiled bodice. Time for another shower and some self-reflecting, he thinks tiredly. ***** When Dean comes out of the shower, he feels strange. Lonely and restless, and he knows exactly what would fix that but shut your face, he isn’t going to text Cas.He does go for his phone, though, and is happy to find a text from Sam instead.
9:32 p.m. [Sammy]:
   You up?
Dean smiles, sitting down on his bed to type out an answer. The bodice is soaking in the sink in the bathroom now, one thing he won’t force his cleaning lady to do is wash his dirty lingerie. 
9:47 p.m. [Me]:
   Ofc
   Just chillin at home

9:47 p.m. [Sammy]:
   Alone?
Dean rolls his eyes affectionately. Sam knows very well that Dean never brings his Daddies home. Although he supposes Sam could assume Dean has invited Charlie or maybe a random hook-up, although the latter has never happened either. Dean gets enough sex from his Daddies, thank you very much. He throws his lingerie drawer a side-ways glance. Well, he used to get enough.
9:48 p.m. [Me]:
   Yeah
   Wanna come over?
That’s where he guesses this is headed anyway. Sam has his own key but he rarely uses it without checking with Dean first, which is unnecessary on the whole but considering how Dean has been acting lately maybe it’s better that Sam throws him a text or call first. He’d masturbated out on the couch just the other day for fuck’s sake…
9:48 p.m. [Sammy]:
   Yeah can I?
   I kinda accidentally lied and said I’ve watched this movie that Jess likes
   Now I need to watch it
That makes Dean laugh out loud. How fucking high school can you be? He shakes his head, typing out his answer.
9:49 p.m. [Me]:
   I gotcha bro
   Which movie?

9:49 p.m. [Sammy]:
   It’s an old one
   The Lake House
Dean snorts. Sam must be really invested if he’s prepared to watch time traveling mailbox love stories.
9:49 p.m. [Me]:
   Damn Sammy
   You must really like this girl

9:50 p.m. [Sammy]:
   Shut up jerk
9:50 p.m. [Me]:
   Just get over here
   Bitch ❤Dean gives himself time to clean up in his bedroom, going so far as to change the sheets himself and air out the room. He almost forgets his bodice in the sink, not that Sam uses Dean’s private bathroom, but still. It of course needs to dry so he hangs it in his shower and hopes Sam won’t spontaneously want to shower in there, for the first time ever. Raiding his fridge he comes up with some cans of beer and he’s just making sandwiches when Sam lets himself into the apartment. He does ring the doorbell first, which Dean thinks is adorable and he finds himself grinning just as Sam walks up to the kitchen island.“I brought snacks,” he says, holding up a bag of Doritos, sounding somewhat confused, presumably at Dean grinning like the fucking Joker. “You okay?”“I’m great,” Dean says and means it. He loves hanging out with Sam and he is stoked Sam immediately turns to him for help with something like this.Of course he wants Sam to branch out and get friends and lovers independent from him, but Dean is used to being needed and he isn’t quite ready to let go of that just yet. So, with that in mind, he is more than happy to pamper his little brother and to watch movies with him so that he can impress this girl he really likes. Except perhaps this movie might be the straw that broke the camel’s back.“It’s, uh, very long,” he comments after what feels like an eternity.“Just normal movie length,” Sam says with a shrug that implies he is just as restless as Dean.Granted, Sam isn’t as much into horror or action flicks as Dean might be prone to be and he has been known to enjoy the occasional foreign movie but this might take the cake.“Tell me about Jess,” Dean says when the mailbox gets more action than Dean himself. “Did you have a good time at the museum?”“She’s great,” Sam mumbles, eyes glued to the TV but attention clearly not on the movie. “She makes me feel safe.”Ah, so the opposite of Ruby, then. Good, Dean is happy.“Awesome,” he grins, poking Sam on his thigh. “So you done it yet?”Sam sighs as if Dean is absolutely insufferable and he’s not wrong. But hey, it’s the privilege of being a big brother, he thinks.“I wanna do it right.”“Not that many ways to do it, Sammy boy.”Sam rolls his eyes and Dean grins so hard his cheeks hurt. They have both stopped paying attention to the movie, making all of this kind of counterproductive but Dean doesn’t mind. “You know what I mean,” he crosses his arms, making himself look small on Dean’s couch and an overwhelming need to hug him comes over Dean. “I don’t wanna do that again. Like what I did with Ruby. I felt like shit afterwards and she hasn’t spoken to me since.”Dean scrunches up his face, hating his little brother hurting in any capacity. “Maybe that’s because I barged in and whisked you away. I’m sorry.”“Nah,” Sam sighs, turning to stare really hard at the TV, as if forcing himself to focus. “I just think they’re a bunch of assholes. I don’t know what I was thinking.”“Better with this Jess then,” Dean says encouragingly. He has only met her once but he really liked her, and he met Ruby once too and disliked her, so there’s that. “How did you two meet anyway?”“Brady has club activities with her,” Sam grins, all proudly and shit.  Brady is Sam’s best friend at college and if he likes her enough to introduce her to Sam, Dean thinks she’s probably great. “Debate club. She’s really fucking smart.”To be honest, Dean wouldn’t expect anything else from a girlfriend for Sammy but he doesn’t say that, mostly because calling Jess Sam’s girlfriend might be going too fast.“So she’s smart and makes you feel safe, that’s gold right there.”“Yeah,” Sam looks pleased. “I even catch myself smiling dumbly when she sends me silly text messages,” he turns abruptly to Dean, surprising him. “Like you do when Cas texts.”“That’s good, I’m happy for you—hang on a minute,” Dean frowns at Sam’s cheeky grin. “I don’t smile dumbly when Cas texts.”“You know you do.”Dean shoves Sam on the shoulder. “Shut up and watch your movie. Actually,” he reaches for the remote, rewinding. “We missed some important parts, I’m sure.”“Dean, no.”“It’s only fair,” Dean says, talking over Sam’s groan. “You watch this like a good boy and I’ll make some popcorn.”“We already had Doritos and sandwiches,” Sam calls after him when Dean slips off the couch, very ready to escape the movie. It’s Sam that has to watch it for his girlfriend anyway, no reason Dean should have to suffer.Besides, Sam deserves it for spouting nonsense like Dean smiling at Cas’ text messages. If anything, he’s laughing at the man for using emojis like a teenager. Cas is a grown man for fuck’s sake. Successful, rich, and influential, not someone who usually would put silly non-relatable emojis in every other message.In fact, just to prove how silly Cas is, which is the only reason Dean maybe smiles sometimes, he shoots off a text to Cas right then and there.
11:23 p.m. [Me]:
   Sammy just said the stupidest thing
He doesn’t even have time to finish his second message before Cas responds, as if he’s fucking glued to his phone.11:23 p.m. [Cas]:
   What? 🧐Dean snorts. See, Cas just proved Dean’s point without any further prompting. A fucking emoji with a monocle, it doesn’t even make sense! 
11:23 p.m. [Me]:
   That your messages make me smile
Unless Cas means it more like a person with a magnifying glass? Oh, so like an investigator, since he asked a question! Heh, that’s pretty clever, Dean thinks, grinning.11:23 p.m. [Cas]:
   Is that so?
   Tell me more 👀Okay those eyes are funny, Dean’s not going to lie about that. And he does like having Cas’ eyes on him. Wait, tell him more about what? What the fuck did Dean just write?!“So, did you go in here to escape the movie?” Sam asks, apprehending Dean and scaring the absolute fuck out of him. “Because you know you make popcorn in the kitchen and not the bedroom, right?”Oh shit, when did Dean go to his bedroom? “Uh…”Sam grins, leaning against the doorframe. “Or did you escape my very true accusations? Because you know you’re just admitting to it smiling like that?”Dean looks from Sam, down at his phone where Cas’ last message is still waiting for an answer, and then up again.“Uh, no,” he says, turning abruptly. “I gotta go take a dump, watch the movie without me.”“Don’t bring your phone in there,” Sam laughs just as Dean shuts his bathroom door. “That’s how you get pink-eye!”Ignoring him, Dean brings up his phone, tapping out a quick message.
11:27 p.m. [Me]:
   Nvm it was stupid
   Ignore me
Great, now he sounds like a fucking teenager himself…11:27 p.m. [Cas]:
   I miss you too, sugar pie
   I’ll see you soon ❤Will he? Will they meet soon? Dean can’t help it, he has to bring up his calendar and check and no, it’s depressingly long until he has a scheduled appointment with Cas. Unless he tries to squeeze him in…No. Dean closes his eyes, drawing a steadying breath. He needs to stop indulging this fantasy, it’s not healthy and it’s not good for business.
11:29 p.m. [Me]:
   Yeah
   Night Cas

11:29 p.m. [Cas]:
   Good night, Dean
Dean spends the rest of the night pretending he isn’t affected by how fast Cas had answered him, and that he had admitted to missing Dean. Because Dean doesn’t care, because Cas is just another Daddy, and that’s a fact.

----- CHAPTER BREAK -----

Sam spends the night, which Dean kind of absolutely loves. He is deep in his confused state right now and being alone wouldn’t be good for him, he thinks. He kind of hates that Cas has put him in this state of mind and he hates even more how fast it has gone. Was it really Monday of this week that Cas proclaimed to want to be Dean’s number one Daddy? Feels like a fucking lifetime ago.He has been sleeping with Cas for the last year or so and things have been fine. Sure, he has always loved his dates and sex with Cas more than his other Daddies, but it’s kind of expected or at least understood that he wouldn’t have a favorite, right? He even plays it up with all of his Daddies, telling them they’re the best. Well, okay, he has never actually said that to Cas before he went and blabbed on Monday and maybe that’s because it would make it feel too true, as if it actually means something. And yeah, he kind of stopped playing those games with Crowley when he looked Dean square in the face and said “no I’m not” when Dean said he was the best out of all of them.In fact, he had followed up with “I might have been at one point, but I for sure am not now. And that’s okay”, as if that clarified anything. Dean hadn’t bothered pursuing any kind of explanation at that time but now that he thinks about it, hadn’t that happened around Sam’s birthday? So like about six months after Dean started seeing Cas too. Cas, the last to join Dean’s lineup of sugar Daddies, and still the most impactful. Or so it seems.Dean can’t really wrap his head around what’s happening right now and he is partially, slowly, coming to the frightening conclusion that maybe this involves love, and that he has never been in love before. He feels stunted and stupid and at the same time he can’t help but feel an incredible joy when he thinks about Cas. He feels elated and as if he wants to smile for no reason.So yeah, he is now completely confused and very happy for the distraction that is his beloved little brother talking about his classes as Dean makes them breakfast because screw his regular morning routine. Most of what Sam talks about goes over Dean’s head but he does understand two things. The studies are exhausting but very interesting, and Sam is both the most tired and the happiest he has ever been. Dean just smiles and nods when Sam talks about one particular professor who seems to have enthralled the whole class. Fuck he wishes dad could see Sammy now. Dad wasn’t always the best of parents but he did always want Dean and Sam to be happy. In fact, one of the last conversations Dean had with his dad before he passed away had been about how sad he was that he hadn’t managed to save more money, for them both to go to college without trouble.“I failed you,” he’d rasped, body broken and ravaged by the cancer that had consumed him. “I wanted so much more for you in life.”Dean hadn’t had any words then, too young and overwhelmed by the situation but truthfully he might not have had any words now either. Because what the fuck was he supposed to say? Yes, dad hadn’t done a great job before he got sick but their situation hadn’t been great either. Plus mom broke his heart when she left, Dean might have been only four years when it happened but he still remembers it as if it was yesterday. It’s sadly the only childhood memory that has etched itself in his mind. How he sat on the stairs, little hands grasping the poles on the banister as he listened to his dad plead with mom to stay, to give them another chance, to love them like they loved her.But mom had tired of playing house and now, with another baby, the burden had only gotten harder and she didn’t want it anymore. Dean remembers feeling for a long time as if it was his fault mom left, since it was his introduction into their lives that had first changed everything.Dad never made him feel as if that was true, though, and he was very adamant that Dean and Sam were precious and his brightest and best accomplishments in life. So it didn’t matter much to Dean that dad sometimes couldn’t feed them because he spent too much money on booze, or that he failed to pay the bills sometimes. And later, when they had lost the house and lived in that cramped apartment and dad got diagnosed with gastric cancer and was dying a little every day, Dean never resented having to take care of both him and Sammy, because dad had made Dean feel loved.When dad eventually died and Dean took Sam to go to California, he never even tried to contact mom to tell her what had happened and to this day Dean doesn’t regret that. In fact, sometimes he entertains the idea that mom has tried to find them and is regretting how things turned out, although he doesn’t think that’s very plausible.“So anyway, you wanna catch a movie tonight?” Sam brings him out of his reverie and Dean can’t help but smile at how easily his little brother can dispel his gloom. “I think there was a new movie Charlie wanted to see? I could, uh, bring Jess. Maybe?” he looks down, pushing scrambled eggs around on his plate and fucking hell, is he blushing?Dean laughs and comes around the kitchen counter to the bar stool Sam is sitting on, ruffling his hair and grabbing his face to hold him still so he can kiss him on the cheek before he escapes.“I would love to,” Dean beams at Sam’s indignant “hey!”. “But only if we catch an early movie. I have a party to get to tonight.”Sam frowns. “With one of your Daddies?” he mumbles and then instantly perks up. “With Cas? You could bring him too, Charlie said he’s nerdy too. I bet he’d like this movie.”Dean snorts. “As if I would invite him to a movie with you guys.”“Why not?”“Why not?” Dean mocks, grinning at Sam’s deepening frown. “Would you invite one of your professors? No,” he answers before Sam can. “It’d be like inviting my boss, that’s why.”“Your boss you sleep with,” Sam counters grumpily.“That’s right,” Dean says, shooting finger guns at Sammy, refusing to admit that he sometimes feels more like a whore than a classy sugar baby. “And to answer your question, no it’s not Cas. It’s actually Michael and I’ll have to be back here at around seven to get ready in time. You think the movie runs that early?”“I’ll check,” Sam says eagerly and Dean kind of wants to kiss his cheek again, reminded of the little cherub he’d been when he was a baby, but he holds back.Turns out the movie of course doesn’t have a showing that early but Dean spends an enjoyable day with Sam and Charlie at her internet café anyway. They play games and joke around, and Dean helps with baking some pastries while Sammy mans the counter for the first time, earning himself some money for the day because Charlie is cool like that.By the time evening rolls around, Dean drops Sam off at the sorority house where Jess lives and is completely normal about it and not at all an annoying big brother — but don’t fact check that with Sammy. And then he drives home to his empty apartment which he has lived in for several years and has loved and that he now kind of dreads.The emptiness suddenly looms in a weird way and Dean feels creeped out by his own feelings. He wants badly to text Cas, just something silly, because he always answers. Always there for Dean, just out of reach but still so close.He of course doesn’t, and instead hops in the shower to get ready. He shaves, all over, and loosens himself up a bit, just to make sure he can take it quickly if Michael wants it. He considers wearing a plug because Michael always gets riled up after parties where people have ogled Dean and been jealous of their supposed relationship, and this seems like a party where that is inevitable.It's a rooftop party with an open bar, not in the name of charity or something like that, but from what Dean has understood this is hosted by some of Michael’s friends and colleagues. That isn’t to say this won’t be a large and extravagant party, all of Michael’s parties usually are. He’s not the kind of guy who would come to Charlie’s café and play board games while having a couple of beers, that’s for sure. Not like a certain someone…Dean sucks on his teeth and decides against wearing the plug for the party but he slips one in as soon as he is out of the shower, to wear while he gets ready. He chooses a smaller plug for that but even so he can’t help but feel a small wave of arousal as he slips in it. Fuck yeah that feels nice, especially when he wriggles his hips a little and the plug presses gently against his prostate. To be honest, he if did live with someone, he wouldn’t mind spending a day at home wearing a plug and being at a comfortable level of aroused until his lover came home and took out the plug to fuck him nicely and slowly.Dean swallows, eyes closed as he fondles his dick, imaging sitting on his knees and waiting for Daddy. Pleasure shoots through him and he sinks to his knees without really thinking about it, facing the bedroom door with his legs slightly spread, ass clenching around the plug.“Fuck,” he mumbles, opening his eyes to look at the open door that leads out to the empty hallway outside his bedroom. “Fuck, yeah okay.”He’s just about to start stroking himself, completely immersing himself in the fantasy, when his phone dings with an incoming message. Grumbling, he gets to his feet and over to the drawer where he left his phone to find a message from Michael.It states that he’s sending a limo to pick Dean up and that it will be at Dean’s apartment in an hour. Dean groans. That’s more than thirty minutes early, giving him no time to take care of himself. Fuck Dean’s life, really.In a fit of petulance, he goes out to his kitchen, stark naked and still with the plug in, to have a shot of vodka. And then another one for the road.And then he goes back to text Michael that that’s absolutely perfect and that he can’t wait. To dispel his bad mood, he puts on his favorite playlist and blasts it while he gets ready.Since the sheer shirt Michael has picked out for him is black and has a sheen of sparkle to it when Dean moves it into the right light, he decides to put on some makeup. Dean doesn’t really do that a lot, mainly because he isn’t really interested in it and neither are his Daddies, as far as he knows. But sometimes he will put on some mascara to enhance his lashes and some lip-gloss to make his lips look more inviting. Tonight he also adds some black eyeliner that he purposefully smudges to give his eyes that smokey look without actually using eyeshadow.He looks good, he thinks, eyeing himself in the mirror he brought out to the kitchen so that he could do his makeup there, in reach of his vodka bottle. He celebrates his appearance with another shot, making him pleasantly tipsy, and then goes to put on some panties. Because Dean is feeling a little so-so and making himself pretty usually helps improve his mood and he looks damn sexy in these lace panties. They’re also black, to match the shirt, not that Dean thinks Michael will appreciate the effort.He rummages around for quite a while for a pair of pants he thinks will fit with the shirt. It’s loose and long, with long sleeves. If Dean was shorter, it could almost pass as a very short dress but since that’s not the case, he goes for something to play into the illusion without being too obvious about it. What he comes up with are a pair of burgundy velour pants with a satin lining.They hug his ass something fierce and they cling to his package, showing off everything, or enough to get the imagination going. They’re long pants but Dean isn’t afraid Michael will miss the sight of Dean’s naked thighs because these pants show them off enough anyway. Looking himself over in the mirror he feels like a proper hoe, but a comfy one and he thinks that’s just right, for a date with Michael. It’s a far cry from the tailored suit that Crowley gave him, or the corset vest he showed off to Cas, but Dean doesn’t do this for his own sake. No, he caters to the needs and wants of his Daddy of the evening and Michael loves it when Dean dresses up in clothes Dean would be caught dead in on a normal day.With all the messing around with the pants, Dean is in danger of running late, and he only realizes when he’s half-way down in the elevator that he still has the plug in. Fuck, it’s so small and comfortable he fucking forgot it was there. Checking the time — on his phone because Crowley’s watch is too valuable to Dean to waste on a party like this — he immediately sees that he has no time to do anything about it and he’ll just have to live with the plug in there.Either he’ll go to the bathroom first chance he gets at the party to get rid of it, sacrifice it to a trash can, or he supposes he can keep it in as a “surprise” for Michael. Although considering how things like that have worked out in the past, he thinks it’ll make Michael cream his pants before they get to the good stuff… But maybe that’s for the best anyway, since Dean isn’t interested in sleeping with Michael tonight, no matter that he’s so horny he’s in danger of popping a boner with just the slightest of stimulation.As it turns out, the limo is already there when Dean exits his apartment building but to the chauffeur’s credit, he neither mentions Dean being late or comments — or even looks twice — at Dean’s appearance. He just opens the door, inviting Dean into the limo, and Dean climbs in with a grateful “thanks”, ignoring the sensation of crawling into the darkness of a giant maw ***** The chauffeur thankfully has the partition up the whole ride and Dean fiddles a little with the buttons in the backseat, by now familiar enough with Michael’s limo that he knows how to put on music. To dispel gloomy thoughts, he turns on some disgustingly positive pop song and hums along, allowing his mind to go blank. He knows there is a liquor cabin back here too and he does eye it, knowing full well Michael doesn’t mind if Dean has a drink without asking. But combined with the vodka he might get too tipsy before even getting to the party and that’s bad for two reasons.One is of course that that wouldn’t be professional of him. While his Daddies do enjoy having a drink and getting drunk together with Dean, none of them want him to get black-out drunk and possibly embarrass himself or them, or for an accident to happen. That goes without saying.The second reason has more to do with Dean being cautious. Because while he trusts his Daddies to be nice to him, even Ketch who sometimes is too rough in bed, he doesn’t trust people he doesn’t know. And frankly, with the mood he is in tonight he doesn’t even trust himself. Wouldn’t want to start bawling for no fucking reason, for example.Lost in thought that not even Taylor Swift can pierce through, he brings out his phone and thumbs through his messages. Of course he stops at his latest conversation with Cas, because Dean is a dumbass like that. He doesn’t know what it is but he just can’t get Cas’ words out of his mind.“One day it will be true, sugar pie. I will be number one for you.”That’s what he’d said and Dean just can’t stop fucking thinking about it, to his dismay. It’s messing with his head and what’s worse, if it even can get worse, is that Dean doesn’t even know if Cas was serious. He sure sounded serious, and then there’s that phone sex they kind of accidentally had. That had felt real and serious too.Dean is so occupied with imagining what that would be like, if it was true like both Charlie and Sammy have insinuated, that he doesn’t even notice the limo stopping. He sure as fuck notices when the door opens, though, and he startles so badly he almost drops his phone but manages to lock the screen just in time for Michael to climb in.He looks pleased as pie to see Dean so maybe it’s okay that Dean didn’t have time to put on a giant smile or strike a sexy pose. Fuck it, he thinks and lunges himself at Michael, he’ll just play into his very real surprise.“Daddy,” he purrs, completely ignoring the way the butt plug presses in delightful places when he moves. Instead he wraps his arms around Michael’s neck and pulls him in for a hungry kiss that’s only half fake. “I was just checking your messages. I missed you.”“I’m here now, baby,” Michael murmurs sweetly, hugging Dean tightly back, stroking a hand down Dean’s back to land it on the swell of his ass. “And you wore the shirt.”“Of course,” Dean chirps and pulls out so that he can preen for his sugar Daddy. “It’s so pretty.”“Not as pretty as you.”“Naturally,” Dean smirks, earning himself a chuckle. Good, Michael seems to be in a great mood, which definitely bodes well for the evening.It’s always easier for Dean if his sugar Daddy is already happy. Then all he has to do is cater to their needs and usually that’s the easy part. The way Michael pulls on him jostles the butt plug again and Dean kind of almost fucking moans. It feels good and no matter that Michael is Mr. Quick Draw McGraw over here, he is also a good kisser and Dean doesn’t mind making out with him during the ride to distract himself.It's blessedly short, though, and Dean feels he has himself enough under control that he doesn’t have to worry about a weird boner poking people’s eyes out. Michael has to adjust himself but that’s pretty much to be expected. Dean is that good, after all.“What kind of party is this, Daddy?” Dean asks when they’re in the elevator ride up.The lobby of the place was fancy, with marble and shit like that, but some of the people Dean saw getting on another elevator before them looked less classy than what he had expected. And considering his own clothes he thinks he fits right in with them, if not the venue.“It’s just a little get-together with Marcell,” Michael says, smiling. “You remember Marcell?”Dean for sure fucking doesn’t. “Absolutely. How fun.”Michael has a lot of strange fashion industry friends and Dean is good at his job, but he’s not that good. Just like with Joanne and her fashion show or whatever a few days ago, Dean is fumbling in the darkness here too, trying to remember Marcell. But it’s okay, he thinks as they exit the elevator, he’ll make it work. He always does.The elevator opens up to the top floor, which is full of what Dean now can tell are little offices. It reminds him of Cas’ architecture firm, with a corridor leading off to the left into the office area and some restrooms near the elevator. Good to know, Dean will have to try and escape down to those to get rid of the plug, and soon. It feels way too good to have in while walking around.There’s a person manning some kind of improvised coat room too, but Dean and Michael just breeze past them to the stairs leading to the roof. There is loud music and the sound of people talking coming down from the open door at the top and Dean wonders disinterestedly if this Marcell possibly works in this building for him to be able to rent out the roof.When they finally reach the party, he stops wondering much of anything and instead tries to relax. Someone has really outdone themselves with decorations, making the whole scene seem like something taken from a tropical beach cabana rather than a rooftop in San Jose. There are palm trees and wooden structures, some of them hosting a bar and some kind of kitchen, and some offering secluded spots to sit and eat and drink or do other things. There are lights everywhere, some hanging, some on strings, and they cast a soft yellow hue on everything, mimicking sunlight that Dean thinks will be really nice as soon as night falls.The spirits are high up here and Dean feels himself getting pulled along with all the happy smiles and good drinks. He accepts one from Michael without thinking, finding out too late that it’s a Mai Tai or something else sweet like that. Not Dean’s favorite but then how would Michael know? It’s not as if he has taken the time to actually get to know Dean. Still, booze is booze and the drink isn’t awful.He downs it perhaps a bit too fast as Michael drags him around the party, introducing people Dean has no interest in getting to know and who will surely forget him as soon as he leaves. Or else remember him as Michael’s side piece. He smiles and makes nice anyway, of course, and he manages to have a pretty good time for a while.And then Michael says, “Oh Gabe, I didn’t think you’d make it!” and Dean’s whole evening takes a sharp left turn into Forbidden Fruit Land.Because there, right beside this Gabe person is fucking Cas. Motherfucking Castiel Novak of all fucking people. Looking right at Dean with those intense goddamn eyes. Sweat instantly breaks out all over Dean’s body and he stalls so damn hard he almost doesn’t hear what the other men are talking about.“I know,” Gabe says in a lamenting tone. “So much work lately and it took me some time to drag my date outside too.”He elbows Cas at that last part and that sure as fuck snaps Dean back to reality. What date now? Cas cuts a look at Gabe, truly breaking his spell on Dean and fucking hell, Dean can believe this is happening.“Well then, happy to have you,” Michael says jovially, as if he is the host, extending his hand for Cas to shake.Dean feels his stomach swoop at the sight of his two sugar Daddies shaking hands and he can’t stop staring. Fucking hell, what the fuck kind of situation is this anyway?! All of his sugar Daddies know Dean has more than one, sure, but none of them have ever met, not even Cas and Crowley whose firms have worked with each other in the past. And Dean had planned on keeping it like that because how damn awkward isn’t this? Also, why did it have to be Cas out of everyone? Tonight, when Dean still has that fucking plug inside him.And above all of that, what date?“This is Michael,” Gabe introduces the two men. “And this is Cas.”“Ah, Castiel Novak,” Michael says as if Cas is the kind of hotshot even the fashion industry would know about. Maybe he is and Dean is just too preoccupied with how sexy he is to notice? “Weren’t you involved in the McNair project in Las Vegas?”“I was,” Cas answers with a little half-smile and fuck his voice, really. “In collaboration with Sandover.”“Right, right. Stellar work,” Michael says as if he knows anything about architecture. Does he know Cas is one of Dean’s sugar Daddies after all and now he’s trying to show off? Dean’s sweating is getting out of hand. “Oh where are my manners? This is Dean,” he suddenly puts an arm around Dean’s waist, pulling him in so that Dean falls against his side, a hand on his chest for support. “My date.”“Pleasure,” Cas murmurs, eyes twinkling.“I’d say,” Gabe exclaims, extending a hand for Dean to shake. “You’re prettier than some of the models here. Or are you actually one of them?”Dean smiles demurely. “Thank you, but I’m only as pretty as the clothes I’m wearing,” he says in the disgustingly sweet voice he has learned to use with Michael. He hates using that in front of Cas, and he can see the man smirking as he takes a sip of what looks like bourbon.“That’s right,” Michael says proudly, turning to kiss Dean on the cheek. “Daddy takes care of you, huh?”Dean wants to sink through the floor. But like the trained monkey he is, he just chirps “Yes”, unable to look away from Cas’ intense stare and not even hearing Gabe chuckling and commenting on Dean’s apparent cuteness.The moment is thankfully broken when a group of five new people descend on the four of them, laughing and hugging, all of them clearly friends with this Gabe guy. It’s enough of a distraction that Dean manages to excuse himself, though sadly not without Michael. No, he follows with a throwaway comment to Gabe and Cas about meeting up later and Dean doesn’t even have to turn around to know Cas is staring a hole in Dean’s back, right through to his fucking heart.Michael babbles something about being happy to have met up with Gabe and Dean wants to snap at him to spend time with Gabe then, since he seems like so much fun. Fun enough that Cas wants to date him, apparently? Because sex with Dean isn’t enough, he supposes.Dean sucks on his teeth, thinking, and something hits him when they’re standing by the buffet table. Maybe Cas was really, truly serious about wanting to be Dean’s number one guy because he wants more out of a relationship than sex and when Dean wasn’t able to reciprocate, Cas moved on? But wait, he hasn’t dropped Dean as a sugar baby, so what the fuck does that mean? He’s using Dean while testing the waters with this new guy?Suddenly Dean isn’t hungry anymore. He needs to get out of here, away from all these people, from the throngs that hide Cas. Needs to get the fucking butt plug out of his ass anyway. But first, a drink to calm the nerves.“I’ll slip over to the bar instead, Daddy,” he murmurs. The word tastes like how glass feels. Sharp and jagged. Unpleasant in a way it has never been before.“Sure,” Michael says, smiling, bless him. “Should I wait here?”“Nah, I’ll find you. I’ll bring you some JD.”Dean mentally slaps himself for that offer. Now he has to actually go to the bar otherwise he’ll look like an idiot, coming back empty-handed. Maybe he can do that first and then blame the drink so that Michael won’t think anything of him going to the restroom.In line to the bar he realizes he’s acting like a proper dumbass now because how the fuck would Michael know which order Dean did things and even if he noticed, what would he care? As if Michael would be mad that Dean had to spontaneously take a piss and did that first.Groaning, annoyed with himself, he rubs his temples. And that’s when he feels a presence behind his back, making the nape of his neck tingle.“Got a headache?”Dean jumps at the sound of Cas’ voice so close to his ear. The motion makes him clench around the butt plug and fuck, that presses in all the right wrong places. With legs like fucking jelly, he turns to Cas, who’s standing right behind him.“Did you follow me here?”Cas blinks and Dean doesn’t blame his confusion. That was a weird fucking question. How the hell would Cas know where Dean would be tonight? “I swear, I did not,” Cas says then, his secret little smile in place to make Dean’s stomach squirm pleasantly. “It’s just the happiest coincidence I’ve had in a while.”“Happy because you like to see me in a state of panic?”“Is that my fault?”Dean grimaces. “Don’t sound so happy about that. Not when you’re here with a date.”“Date?” Cas repeats dumbly and then has the audacity to chuckle. Fuck him and how his sounds make Dean’s body react. He can’t stand here in the middle of a crowded rooftop and get a boner but his dick tries to prove him otherwise. “You can’t believe everything Gabriel says. We’re just colleagues, and childhood friends. No,” Cas shakes his head. “Even if I had been interested in him, Gabriel is all for the ladies. And besides,” his eyes darken, voice going all enticingly rumbly. “Why would I look at someone else when I have you?”Dean’s whole body is on fucking fire. “So he’s not your…?”Cas shakes his head, leaning in and looking like he wants to touch Dean. A fine tremble goes through Dean and he almost gives in, overwhelmed by the relief he feels that Cas is still single.“But don’t you worry, sweetness,” Cas murmurs, barely audible over the music and the crowd. “Daddy respects your boundaries.”Fuck it. All Dean wants is for Cas to overstep them all. To fucking bulldoze them down, grind them to dust. Force down all Dean’s walls and sweep Dean away. Whisk him into the night and never return him. But he won’t, they can’t.Right?“Good,” he chokes on that one word. “Thank you.”“Anything for you, sugar pie.”Yeah, no fucking way Dean is staying in line after that, fuck having a drink and fuck Michael’s JD. He slips away on shaky legs, goes to find Michael and snuggles up to him in a way that makes Michael drop everything and pull Dean into a little corner behind some palm trees. There they make out for a while, Dean desperately trying to override the rampaging thoughts in his mind, without success.They’re interrupted when a friend of Michael’s happens upon them and they laugh it off, instead spending some time with that friend and her date. All the while, Dean is hyperaware of the fact that Cas is still somewhere here and he can bump into him at any point. He knows he won’t be able to control himself if he does. What he had hoped to accomplish by sucking faces with Michael he doesn’t fucking know because all it did was make him more aroused. He really has to get that fucking plug out of him now.“Restroom,” he murmurs when Michael drags him to the bar for that forgotten JD. “You can order without me.”Michael kisses him goodbye for now but seems quite content with staying with his friends and Dean thanks the fucking Gods for that because knowing himself he might need to jerk off now. His whole body is thrumming with desire, only not for the man he is with tonight, and he has to force himself to not think about anything as he more or less thunders down the stairs to the restrooms by the elevator.The area thankfully seems somewhat deserted and Dean rushes into the men’s room, heart pounding. He slams the door behind himself, leaning against it with his eyes shut, breathing out. Finally, peace.“Dean.”His eyes immediately fly open at the very familiar voice.Peace unless, of course, he runs right into Cas.

----- CHAPTER BREAK -----

The first thing he sees is Cas because of course it is.The restroom has a line of urinals on one side of the room, stalls at the far backend, and a line of sinks opposite the urinals and that’s where Cas is, washing his hands. He looks like he is surprised to see Dean and as if he expected to run into him all at the same time. Fuck he looks good, too good to Dean right now, and he can feel a fine tremble go through his body when Cas straightens and dries off his hands.Those hands have been on Dean’s body — holding him, caressing him, pleasuring him — so many times now. Why the fuck is he this affected by the sight of them right now?His ass clenches and sudden clarity comes over him. Right, the butt plug. That’s totally the only reason. Because it has made him so aroused, especially after his make-out session with Michael. Yes, logical.“Are you alright?”No, Dean is far from alright, Cas. His mind is a jumble and his body feels feverish. Also, these fucking pants and the panties don’t hide anything and he’s so dangerously close to getting harder than the semi he is already sporting.“Y-yeah.”Two strides, that’s all it takes, and then Cas is over by him. Then Daddy has one hand against the wall over Dean, leaning in. Close, so close.Dean's breath shudders out of him when Daddy squints at him.“Never lie to me, sweetness.”Dean’s dick is filling out right now, and that’s the truth.“I have a butt plug in,” he whispers, eyes big, catching every subtle shift on Daddy’s handsome face. “I need it out.”“You have it in for him?”“No, he doesn’t know,” Dean makes an embarrassing eep-sound when Daddy grabs his chin. “Don’t get so close.”“You’re the one pulling me in,” Daddy rumbles right against Dean’s ear and he’s right, of fucking course he is, because here Dean is fisting the lapels on Daddy’s suit jacket. He moans pathetically.“You’re gonna make me hard.”Daddy breathes out sharply. Dean’s body strains, desperate to have more, they’re already so close, close enough to kiss and Dean needs it, needs his Daddy to—the sound of someone flushing in one of the stalls makes them both jump.Dean stares at Cas with big eyes, mind racing along with his heat. “Daddy…”Cas’ grip on his wrist is hard as he drags Dean out of the restroom and along the corridor outside and Dean hopes it will leave marks. Wants to see imprints of Cas’ fingers on his skin for years to come.They walk quickly, Dean beyond the point of someone noticing his boner, but though a few people see them and smirk knowingly, no one really says anything or stops them. It’s a party, after all, and everyone is either drunk or worse and no one will really think twice about two men running off together.Well maybe someone will think about it if they recognize Dean as Michael’s date but that’s far from Dean’s mind right now. Instead, all he can focus on is Daddy’s broad back and the way he holds on to Dean, as if he is afraid he will spontaneously evaporate. Desire is coursing through him and he can barely keep his baring. He knows they’re still in the same building, still on the same floor as the restrooms and the coat room, but he only realizes Cas has been looking for a secluded room when they eventually stop outside what looks like a storage room for office supplies.“Careless,” Cas mutters under his breath when he tries the door and it turns out to be unlocked.Realistically, logically, he is of course right. Who the hell leaves a door to a storage room unlocked on the night the roof is rented out for a whole ass party? Dumb.But Dean is far from complaining, or even commenting. Not when Daddy drags him inside the room, flipping on a switch and then pressing Dean up against the wall beside the door, locking it without even looking. No, Dean is really fucking satisfied right now and when Daddy steps in, he eagerly wraps his arms around the other man’s neck, pulling him in for a deep kiss.Or maybe it’s Daddy kissing Dean now, he doesn’t know and doesn’t care. All he can register is pleasure when Daddy’s tongue wraps around his, licking possessively into Dean’s mouth, and their groins grind together. The way the lace panties drag against his dick feels fucking divine. Dean is so hard already that the littlest friction makes pleasure pulsate out with each bump and grind, and when he feels Daddy getting hard too, he moans right into the kiss.“Please,” he gasps, clinging desperately to his Daddy. He thrusts against him, looking right into his eyes. “Feels so good…”“Sweetness,” Daddy rumbles, a smirk coming over him, making Dean shudder. Daddy always takes such good care of Dean but sometimes there is a slightly sadistic streak inside him that pops out and Dean fucking lives for those moments. “You’re tempting me.”Dean whimpers when Daddy puts his big hands on Dean’s ass, groping him, pulling him in so that they can grind harder. His kisses are deeper now, slower and more meaningful and Dean’s mind is reeling. His dick strains inside his panties, balls throbbing and fuck, fuck, that goddamn plug is pressing in all the right places.“P-please,” he moans when the pleasure is getting unbearable. It’s so good but the plug is too small and so it’s too little at the same time. And Daddy is right there.Daddy cups Dean’s cheek, holding him back when Dean wants to lean in for more kisses. Arousal flares hotly in Dean’s body and he looks up at Daddy with hooded eyes. For a moment Daddy only looks down, meeting Dean’s eyes, and the very air between them, around them, feels electric. Dean is trembling, needing so much. He is leaking into his lace panties and pleasure dominates his body right now, making all of him feel sensitive.“It’s bad etiquette,” Daddy eventually says, leaning in to speak the words against Dean’s trembling lips but still holding him back so they don’t end up kissing. “To ruin a sugar baby when he’s out with one of his patrons.” The way he said patrons instead of Daddies makes Dean melt and he doesn’t even react when Daddy turns him so that Dean is facing the wall. “But I can,” he continues in his gravelly voice, so close to Dean’s ear that a shiver goes through his body. “So I will.”Dean chokes out a moan when Daddy bites him on his neck, whole body going rigid. He’s suddenly so close to coming that he doesn’t know what to do with himself. He needs Daddy—needs Cas—and when Daddy starts pulling down Dean’s pants, he can do nothing but help him. “Gorgeous,” Daddy growls, fingers skating over the lace panties. “Such a waste on him.”Dean moans, squirming in Daddy’s arms, pressing his thighs together just as his pants fall off him. They pool around his feet but Daddy helps him step out so that he can lift one leg to get better access to Dean’s ass, simply pulling the panties to the side. They dig in a little but only in the best of ways.Dean’s whole body is shaking now and Daddy’s words keep running on a loop.
But I can, so I will.

So I will.
 I will.Dean has never wanted anything so much in his whole life. Of fucking course Cas can because he’s all Dean ever wants. He’s funny, nerdy, intelligent, and so fucking handsome Dean just about pops a boner simply fucking looking at him. Of course he’s Dean’s number one Daddy, was there ever really any competition?“Still so tight, sweetness,” Daddy groans, lips still against Dean’s neck, licking and kissing the bite mark there.“It’s a small plug,” Dean whimpers, turning his head so that he can look at Daddy over his shoulder, hands against the wall for support. “Just to feel nice.”“Did you need that for tonight?” Daddy murmurs, eyes glinting as he feels around Dean’s ass, fingers dabbing around the rim beside the plug and fuck that feels good.Dean shakes his head, butt canting out because fuck yeah, he loves Daddy’s fingers. “I just wanted it for a little while, when I was getting ready.”“Did you forget it?”“I forgot it.”Daddy’s chuckle gives Dean life.And then he’s not thinking about that anymore because Daddy is pulling off the panties too and those are Daddy’s fingers, deep inside Dean together with the plug, and all he can do is gasp and try to relax to let the man completely in. Dean really wants him inside, don’t make a mistake about that, but fuck he’s so tightly strung that he can’t really relax.“Cutting my finger off, sugar pie,” Daddy rumbles and Dean whines, body sagging.“I-I…”Daddy hums, one hand going up that stupid shirt Dean has on, snaking up and easily finding a sensitive nipple. Pinching it, he makes pleasure blossom and Dean breathes out shakily, ass unclenching and allowing Daddy inside.“How would you do this on your own, hm?”Probably quicker and more efficiently, but not half as pleasantly and Dean wouldn’t have it any other way.“Take it out,” he moans, wriggling his ass. “Want Daddy’s…”Daddy grunts, stepping in to grind his cock against Dean while at the same time pulling slightly on the plug.“I’m just here to help you take it out.”“No,” Dean whines, body thrumming with pleasure. “You promised. Ruin me,” he slurs, drunk on Daddy and pleasure, and possibly some of the booze but fuck those weak drinks. They’re nothing compared to how Daddy makes him feel. The rush he feels when Daddy looks at him just right, or touches Dean’s body in the perfect way.“Rhuin you, was it?” Daddy says mockingly, mimicking Dean’s slurred speech. He chuckles when Dean only arches his back, pressing back and moaning. “You’re far too precious for that, sweetness.”“No,” Dean says again, desperation flaring inside him. “I’m a slut for you, Daddy.”There’s a palpable shift in Daddy when Dean says that, as if he has been in control this whole time and it’s only now that he’s going to act on his impulses. As if Dean’s words have impact, more than just the superficial kind, and Dean can’t say how much that excites him.“I don’t have a condom,” Daddy nearly growls.Dean doesn’t fucking care.“I just want you inside me.”Fuck that plug, throw it in a damn dumpster for all he fucking cares. As long as he can get Daddy’s perfect cock to fill him instead.To his complete, but thankfully short-lived, disappointment, Daddy takes a step back from Dean. But then he’s kneeling and fuck yes, that’s his face close to Dean, one hand still fingering Dean’s ass and the plug, and the other coming around to the front to wrap around Dean’s dick.Pleasure explodes inside Dean and he surges for the contact, fucking Daddy’s hand to the point of almost forgetting what’s happening with his ass. But fuck, how can he not feel the way Daddy eases the plug out of him? It’s just so fucking good, the pleasure almost too much. He moans, legs trembling and ass clenching just as the plug leaves him. The pleasure makes every nerve-ending feel raw now, his whole body consumed by feral desire for the man behind him.“Perfect,” Daddy rumbles when the plug thuds to the floor, finally discarded, and he’s thumbing Dean’s rim. “So pretty for me, sugar pie. Always.”Dean sobs out a broken moan and then Daddy is on his feet again, belt clinking. The hair at the nape of Dean’s neck stands on end and he can’t think, can’t breathe, lives only for this moment when Daddy is pressing the blunt head of his cock against Dean’s greedy hole.“So hard,” he moans, arching his back.“Only for you,” Daddy replies, ruining Dean with that line alone, and then he’s pressing inside.It’s tight, it’s hot, it’s all Dean needs for now and forever. He breathes out, feeling as if everything finally is right in the world. This is how he’s supposed to feel. Safe and loved and so desired he can’t help but embrace the pleasure Daddy’s cock gives him.“Pressing in all the right places,” he gasps, clenching and unclenching, his own dick almost trembling and oh, oh.“Better than a plug?” Daddy chuckles, his cock jumping. Dean’s whole body is throbbing and he is growing fervent, like an exposed nerve, like the desperate bitch he is right now.“Better than anything,” he sobs. “Than anyone.”“Dean,” Cas groans. “You’re going to make me come too fast.”Oh Cas never comes too fast, never before Dean, but it’s okay, more than okay. Dean can already feel it in himself too and it’s so sweet. Feels it gathering, feels that pressure, so pleasant and so persistent.“Fuck me,” he chokes.Daddy grunts and pulls out. Then thrusts back in, and Dean is in Heaven.They rock with Daddy’s movements, in and out and Dean would have fallen if it wasn’t for Daddy’s sure hands holding him. One hand on Dean’s hip and the other on his chest, pressing him back against Daddy. He’s so strong, knowing just how to handle Dean’s body. They come together in waves, Dean’s mind blank now as pleasure takes over, blanketing everything else. His breathing comes in raspy gasps and oh God, he’s so hard, so close to bursting and he just needs that little extra.“Your sounds will do me in.”And there it is. Daddy’s—Cas’—confession, laid bare in a strained whisper, is all Dean needs. His body locks up, eyes open but unseeing as he chokes out a series of “ah, ah, ah” while his dick jumps with every pump, coming untouched. Daddy swears behind him, pressing closer, big body warm against Dean’s back, and it doesn’t take much longer until Dean feels Daddy’s cock jerking.Daddy breathes out harshly against Dean’s neck and Dean is fucking dying to kiss but Daddy sinks to his knees as soon as he has pulled out. Dean only knows this because Daddy has his hands on Dean’s hips, holding him still, and when he feels Daddy spread his cheeks, he doesn’t know what to fucking do with himself.“What—?”“Can’t have you return like this,” Daddy rumbles and then proceeds with short-circuiting Dean’s brains because that’s his lips, that’s his mouth, on Dean’s ass. And not just for a regular rimjob, no.That’s Daddy licking and sucking his own come out of Dean, completely eating him out.Dean whimpers, trembling, overwhelmed by emotions and feelings, overwhelmed by how his body responds to Cas. It’s intoxicating, it’s frightening in its intensity, and Dean doesn’t know what to do with his racing heart. Or these fucking realizations.“There we go,” Cas says when he is finished, sounding way too fucking satisfied for someone who just sucked his own come out of someone’s ass. “All better.”Dean whips around as soon as Cas is standing again, pulling him into a desperate kiss, no matter the fact that Cas’ lips and tongue were just pressed against Dean’s hole. He simply licks deeply, tasting himself and, more importantly, Cas. Tasting his Daddy directly.“That was…”Words are insufficient. Cas smiles like he knows, knows the depth of what just transpired between them and feels the same, Dean knows this from seeing that smile alone.“I know,” Cas murmurs, giving Dean a last kiss before stepping back and bending down to pick up the butt plug. “And you know how I feel already.”Dean’s heart constricts painfully. “Cas…”He can’t believe he’s standing here with his pants off and talking with Cas about fucking feelings of all things. After getting his ass fucked raw by the man. At a party where his sugar Daddy is probably looking for him. Well, his sugar Daddy of the evening…“Yeah,” Cas says, smiling of all fucking things. He holds up the butt plug. “I’ll take this, if you don’t mind?”Actually Dean doesn’t mind because that just means less eventual questions for him to answer but what the fuck will Cas do with that?“Just throw it away.”“No,” Cas smiles and wraps it in his pocket square, pocketing it. “I think I’ll find all kinds of delightful uses for this in my spare time.”Dean’s body flushes hotly, cheeks burning. “You…”Before he can continue, Cas leans in to kiss him. It’s surprisingly chaste compared to what they just shared, but Dean melts all the same.“I’ll see you next week, Dean,” Cas murmurs, winking as he pulls away.Dean wants to weep because all he fucking actually wants is to follow Cas home. To be allowed into the man’s apartment, arms, bed. To be enveloped in his warmth and love, to be Cas’ number one just as Cas wants to be his.But instead he has to return to this goddamn party, all ruined like Cas promised, and pretend to be interested in what Michael has to say. The thought is depressing enough that he just stands there when Cas slips out of the storage room. He thinks he detects a slight hesitance in Cas’ movements but neither of them acknowledge it. Dean knows very well that Cas wouldn’t leave Dean like this if circumstances were different but there is nothing to it now. They can’t go back to the party together, not after leaving in such a flurry.Dean groans as he bends down to retrieve his pants. He feels foolish, nervous that he has messed up with Michael, and above all his body is tired. It’s the pleasant kind of tiredness he usually feels after a great orgasm but combined with a soreness that comes from having sex in a place like this, and a position that he’s unused to. He looks at the stains he will leave on the wall. Some poor schmuck will come in here on Monday to get supplies and will notice that. How disgusting.In a fit of annoyance, he looks around for some paper, finds paper towels for dispensers and rips out a few to dry off the wall. But where to put the rolled up papers now? Nowhere of course because there isn’t a bin in here and he’s not about to walk around with them in his hand.In the end he leaves them on the floor and feels stupid about everything.Rejoining the party is a goddamn chore but Dean grits his teeth and makes his way past drunkards and party girls to find his sugar Daddy. It’s his job and he’s good at it, something he has had to keep reminding himself of lately.“There you are!” Michael exclaims when Dean eventually finds him. He’s standing together with that Gabe fellow and Dean’s insides instantly tingle with the knowledge that Cas probably is close by too. “I’ve been looking.”“I’m sorry, Daddy,” Dean mumbles demurely, slinking in to glue himself to Michael’s side when he raises an arm to pull Dean in. “My stomach is upset.”“Oh?” Michael says, kissing Dean’s temple. “Well you do look disheveled.”No doubt from getting fucked so goddamn thoroughly but let’s not go there. Gabe gives Dean a look up and down and Dean feels suddenly very conscious of the fact that his nipples are on full display under this sheer shirt.“Did you eat something bad?” he asks and Dean gets the sudden feeling that he’s trying to give Dean an excuse. He can’t explain it, maybe it’s in the way Gabe looks at him, but whatever, Dean isn’t about to look a gift horse in the mouth anyway.“Maybe,” he mumbles, nuzzling against Michael in a way he knows this sugar Daddy likes. As if Dean is a cute little baby boy. It works, because Michael coos and discards the drink he had in his other hand on a nearby table so that he can hug Dean more properly. “I did have something with shrimp,” he adds and gestures noncommittally towards the buffet table.”Gabe nods. “Cas said the same thing just now.”“He did?” Michael asks, looking at Gabe and hopefully not noticing how Dean stiffens. How he has to make a conscious effort to relax.“Yeah,” Gabe nods, taking a sip of his drink. Something colorful with an umbrella. It looks kind of good, Dean isn’t about to lie about that, even though he usually doesn’t prefer the sweeter drinks. “He left to go to the restroom and was away for ages,” Gabe grins. “Came back looking all flushed like little Dean-o here and said he was going home.”“And he ate here too?” Michael says, frowning at the buffet table.Gabe shrugs. “I think so. Best avoid the shrimp, I suppose.”The two of them talk a little more about that, Gabe telling them about this time a conference he and Cas had gone to had been canceled because of some bad shrimp, but Dean doesn’t listen at all.So Cas had come back looking flushed, had he? Well, after sex like that Dean supposed it was only natural… But that Cas had gone straight home too? That makes Dean think and he would be lying if he said all his thoughts were pure. Because Cas had done that to Dean, then taken the plug and said he would find uses for it in his private time. Cas, with Dean’s plug, on his way home…“Daddy,” he mumbles, face against Michael’s neck and suddenly very aware of the mark Cas possibly left on Dean’s own neck. “I think I need to go home too.”The look Michael gives him then is for sure one of disappointment and displeasure and Dean feels a wave of guilt come over him. Michael pays a lot for Dean’s company, and he does shower Dean with gifts, but even so Dean can’t bring himself to play this game anymore, not tonight. He feels bad, he really does, because Michael isn’t a bad sugar Daddy. He’s pretty considerate and generous, but he just isn’t Cas. And that’s a fact.“If you’re sure…” Michael starts, sounding as if he hopes Dean will change his mind immediately.But no, Dean has made the decision now and all he wants is to go home and sleep this night off.“I’m sorry.”Michael sighs dramatically and Dean feels very conscious of the fact that Gabe is still standing right there, looking at them having this exchange. What does he think? Does he know by now that Dean is a hired sugar baby or does he still think Dean and Michael are madly in love? And what will he tell Cas? He’ll probably say something about Dean going home early too and Dean doesn’t know how to feel about that, if he wants Cas to know how affected Dean got or not.“Will you be okay by yourself if I call the limo for you?”Because Michael obviously doesn’t want to leave yet, the party is just getting started after all. And shame on anyone who thinks Michael is the kind of considerate man who will sacrifice his own fun for someone else. It’s not like Dean is actually precious to Michael anyway.Perhaps it should be some kind of indication of his feelings that Dean isn’t hurt in the slightest by Michael’s indifference.“I will. Thank you, Daddy.”“Of course, baby,” Michael mumbles absently, his phone already in hand to dial his chauffeur.Dean makes the executive decision to wait down on the sidewalk, pretending he doesn’t feel embarrassed by the clothes he’s in. Well, the looks he receives are nothing short of interested and hungry so he supposes he can feel good about that but he of course doesn’t really.The chauffeur has a hard time keeping a straight face when he eventually comes to pick Dean up, opening the door for him like usual. He has a slightly raised eyebrow, clearly wondering why Dean is going home without Michael.“Food poisoning,” Dean mumbles, gesturing to his stomach, to which the chauffeur nods solemnly. “Please take me back to my apartment.”“Yes, sir.”Feels good to be called sir, Dean won’t lie about that, and he gives the chauffeur a thankful smile before slipping into the darkness in the limo. The drive is uneventful and short and Dean wishes he had some loose cash to give the chauffeur as thanks when he arrives back home but he doesn’t, so he only offers another smile and slips into his building.In the elevator ride back up to his apartment, Dean considers texting Sam simply because he doesn’t feel like being alone right now. And fuck no, he isn’t about to reach out to Cas because considering how Cas just up and left, Dean gets the distinct feeling Cas doesn’t want to talk tonight. Maybe he just wants to be alone for a little while, after the stuff that happened between them? Dean kind of feels the same, even when he doesn’t.In the end he texts Charlie, who of course immediately answers.Instead of texting back to answer her question about how the evening went, he waits until he’s in the privacy of his apartment and calls her.“What’s up?” she answers, sounding happy, and Dean draws strength from her.“I’m tired,” he mumbles, going around his apartment and turning on the lights in a vain attempt at chasing away shadows he knows are only in his mind.“Well it is kinda late,” she says teasingly, making him smile.Putting the call on speaker phone, he walks into his bedroom to undress. The lace panties, usually so pleasant and arousing, feel like they’re chafing his sensitive dick now and he peels them off with a grimace.“I mean I’m tired of what I do for a living.”Charlie hums. “Maybe four is a lot? Feels like you’re always on, y’know? Always someone to please, somewhere to be.”Dean sighs deeply, lying down on his bed in only the shirt and looking up at the ceiling. “Right as usual,” he murmurs. Charlie has never judged him for his choice in work but he does know that she thinks he shouldn’t do it, that it can lead to bad things if he isn’t careful and that she’s worried about him.“Did something happen at the party?”Dean sucks on his teeth while he thinks. She only knows that one of his sugar Daddies was taking him to a party, she doesn’t know where or with who, and Dean isn’t so sure he wants to tell her everything. Not that she knows any of Dean’s Daddies by name or appearance, aside from Cas, since they met in her café and all.“Why don’t you just ask him out?” she had asked after, when Cas had left. “Like on a date. Like boyfriends.”Dean had scoffed. “Someone like that doesn’t want someone like me as an actual lover,” he’d grinned, displaying Cas’ business card like a trophy. “Guys like that get sugar babies and as it happens, I’m the best there is.”She had looked doubtful then but Dean had attributed that to her hesitance about his line of work in general but now he thinks maybe that look had been about something else. Maybe she had seen something between him and Cas that Dean hadn’t back then. And maybe Dean’s eyes are slowly opening now.“I met Cas there,” he eventually says, deciding that he has to talk about this. He didn’t just want to hear her voice, he needed to talk, and he needs to own that need. “He wasn’t the Daddy I was there with.”“Oh shit,” she whispers and Dean can hear that she’s part mortified for his sake and part curious as all fucking hell. “What happened?”“Nothing at first,” Dean sighs. He wriggles on the bed, getting comfortable with his head on his pillow instead. “Cas understood that I was working and he’s really respectful about that.”“And the other Daddy?”“He didn’t suspect anything,” Dean cringes at the memory. “But I nearly fucking died when they shook hands. They apparently have a common friend. He was there too.”“Damn,” she says and yeah, that’s a little giggle there at the end. Probably a nervous one but Dean can’t help but smile a little himself because honestly, what a fucked up situation. “How are you still alive?”“My soul might have shriveled up a little from the embarrassment,” he agrees, but then shakes his head. “I was so fucking nervous. But Cas was like ‘I respect your boundaries’,” he smiles again when she giggles at his bad impression of Cas’ deep voice.“That’s good then! But I get why you’d feel weird,” she breathes in, as if steeling herself. “Especially considering your obvious feelings for Cas.”Dean feels gut punched. Is he really this obvious? Well, yes and no, he supposes. She already knows how he feels so of course it’s obvious to her.“I did something stupid,” he croaks. “I acted on those feelings.”He puts an arm over his face, hiding, when she gasps. “Tell me,” she hisses and Dean pulls his legs up, turning on the side to curl into a ball.“I told him I wanted him and we fucked in a storage room,” he says in a hushed tone. “I’m a bad sugar baby.”“Oh Dean,” she says and he considers the possibility of crying a little but doesn’t really feel sad as much as confused. “You’re not bad.”“It’s a little like cheating,” he mumbles.“How?”“I was there for another man’s sake, right?” he argues softly. “I was his for the night and I went away with someone else and then I pretended I got food poisoning so I didn’t have to have more sex.”“Dean,” she admonishes gently. “You’re not in a relationship with any of these men, it’s not cheating. But okay, I see your point. It’s as if I had an employee who called in sick just so they could go work at another café.”“Yeah,” Dean mumbles and even though the scenario she proposes is also bad, it does make him feel better. “I won’t do it again.”“That’s a good boy,” she says, only a little teasingly and he knows exactly why. It’s not her he needs to apologize to, after all. “But I do think it’s time you started figuring out what you really want, Dean.”“Yeah…” Dean sighs, turning on his back again. The shadows in the corners of his ceiling look less looming now after hearing Charlie’s comforting voice and words. “I’m starting to think you’re right.”

----- CHAPTER BREAK -----

“And then I told Miranda,” Ketch continues his long-winding story that Dean totally stopped listening to about half-way in. “If she thinks she can serve slop like that and still be employed here, she has another thing coming.”Ketch laughs at his own words, as if they were a great joke and not an insult to someone who probably put a lot of effort into her work. Knowing Ketch and his presumably refined taste, Miranda’s food was probably more than okay and far from “slop”, but what the hell does Dean know? He’s just a kid from a podunk town who actually likes McDonald’s.“Good one,” he mumbles, forcing down some of the wine with his steak. It’s very bitter and he doesn’t like it at all.What the fuck he had been thinking planning a Sunday brunch with Ketch, he will never know. Even if the party yesterday hadn’t been a full on disaster, and even if he hadn’t been up all night thinking about Cas and about Charlie’s words, it was still stupid to have brunch after a party night. What if he had had an awesome time and been up until morning, drinking and laughing? Well then he supposes this would have been his hangover food, although what a sad one that would have been.Some steak, admittedly nicely done, with a dollop of cauliflower puree and two pan seared carrots. Sad and dry and shriveled. Dean stares down at his plate, the realization that he actually hates this kind of food dawning on him slowly. And for that matter, what the hell kind of brunch food is this? Brunch is supposed to be an amalgamation of lunch and breakfast. Dean would never eat steak for either. Where are his fried eggs or bacon, or even some goddamn chicken. More importantly, since he was drinking last night, where is his sweaty hamburger and sugary milkshake?Dean wants to go to that burger joint Cas took him to after he ate Dean out in his office, and he wants to go now. He looks up with wide eyes, feeling a pressured urge to just run.“Good, right?” Ketch says, clearly misinterpreting Dean’s wild stare. He gestures to Dean’s plate with his fork. “It’s Kobe beef.”What the fuck even is that? Dean doesn’t care, all he wants is out. Out of this fancy restaurant with their dimmed lights, purple decor, waiters that look at him as if they know he doesn’t belong, and his sugar Daddy who doesn’t care about Dean one bit.“It’s delicious,” Dean hears himself say. Ketch looks pleased and starts talking about various cuts of beef and how his restaurants only have the best. Dean’s pulse is pounding in his ear and he’s not listening, desperately needing to clock out but what can he do? Just quit? Right here, right now?No, that’s ridiculous. He needs to think things through, do things in the proper order. It’s not as if he hasn’t dropped sugar Daddies before, he knows how to do this in a nice manner. Sure, he has been with these four for a long time, all of them except Cas for over two years now, and this is the best set-up he has had since he started this line of work. But back then, when they had just moved and Sam was in his first semester of college and Dean was still trying to figure out how to make dad’s savings and life insurance last them, he had run into some seedier men. Some who just wanted his body, and then some better, who actually wanted him as a professional sugar baby. Alastair was the one who had taught Dean about the actual job but Dean had left him quick enough. There had been others after that, only lasting a few months here and there, and Dean got pretty good at vetting his prospective Daddies, and at judging when enough was enough. And how to get rid of them in a way that ensured they wouldn’t be a problem for him in the future. Hell, he even got rid of that stalker one so he knows he knows how to do this properly.He doesn’t really think that will be a problem, his hesitance is rather born from the fact that he is, well, hesitant. Because what if he drops one or two, or all of his sugar Daddies, and things don’t work out? And what exactly is it that he wants working out? Money? Life? Love? He feels as if he needs to sort through his emotions but that he hasn’t given himself time to do that. Time alone, time with Sam, time to just think and feel and fucking hell, he needs to talk to Cas. It’s his fucking fault everything happened anyway. If he just hadn’t opened his big mouth back on Monday and—Oh God, it hasn’t even been a week…Dean’s spiraling and Ketch’s incessant droning are both cut off when Dean’s phone suddenly goes off. Dean jumps and Ketch frowns. The sound is loud and screeching in the soft ambiance of the restaurant and Dean scrambles to get his phone out of his pocket.“Sorry,” he says, looking down at the screen to see that it’s Sam calling him. That’s not surprising, though, since Dean always has his phone on silent when he’s working and only allows calls from Sam to filter through. “Sorry, it’s my little brother.”Ketch looks annoyed but doesn’t say anything stupid, or try to stop Dean from answering. Dean has made things very clear with every sugar Daddy he has ever had, even going so far as to put in a clause for it in his contract stating that Sammy always takes precedence. That was more important when they were younger but it’s still on the fore-front of Dean’s mind. Especially now that Sam is actually calling when he knows Dean is at work, something he doesn’t really do, normally.“Hiya, Sammy,” he mumbles as he gets up from his chair, walking away from the table to get privacy, or give Ketch a moment to eat his food without Dean talking on the phone next to him, whichever will make him look better later. “You okay?”“Are you, um…” Sam’s not completely okay, Dean can hear it in his voice. “Sorry, fuck, you’re working. Right?”“That’s okay,” Dean says softly, forcing himself to smile so he’ll sound happier. “What’s up?”“No that’s um, I shouldn’t disturb you,” Sam mutters the last part and now Dean knows something happened. Sam is rarely pouty. “Is this about Jess?”“No.”Dean’s stomach twists. “Ruby, then. What did she do?”Sam sighs, clearly frustrated. “I met her, not like on purpose but…” he sighs again. “She had this guy with her. Lucifer. They said stuff so like, I, uh, I know she has been talking about…me.”The way his voice cracks there at the end, on the small little “me”, damn near breaks Dean’s heart. There’s a clinking coming from behind Dean, too loud to be a generic sound from the restaurant. Ketch is clearly getting impatient but Dean doesn’t care.“Don’t worry about that,” he says confidently. “It doesn’t matter what she thinks, or what she has told some other guy. You know your own worth Sammy, and it’s not based on one experience with some stoner girl or a dude with a dork name like Lucifer.”Sam laughs lowly at that. “It did sound kinda doofy when she introduced him.”“Just move on from them, Sammy,” Dean says softly. “It’s not like you hang out with those guys anyway, right?”There’s a second before Sam answers, probably the time it takes him to breathe in, but it stretches in Dean’s mind, lasts eons. He doesn’t want his little brother mixed up with the wrong crowd. He wants him to finish his degree and get a good job, have a nice and normal life with a partner that’s just perfect for him.“No,” Sam answers basically immediately and Dean breathes out, slowly and evenly. “It was just a coincidence that we met now.”“Good. Hey, what do you say you and me meet up for some burgers?” he doesn’t even have to fake a smile now, the idea alone making him feel so much better. “Call Jess too, my treat.”Better Jess than that Ruby, much better. And Dean is sad that he missed out on an opportunity to hang out with her yesterday, all because he had to go to a stupid party with his stupid sugar Daddy and get his stupid brains fucked out by Cas.“Yeah, that would be—” Sam starts happily but cuts off his own words, voice going lower again. “But aren’t you working?”Dean can feel Ketch’s eyes on his back like lasers and he wishes he had gone further away. He’s far enough that Ketch can’t hear him, but he should have left the room too.“I am, but don’t worry about that. They all know you come first.”“Nah,” Sam mumbles, sounding happy about that but obviously unwilling to admit that. It makes Dean smile again. “I feel stupid. I just got a little messed up, but I already feel better.”“Well, I don’t,” Dean states, taking the decision off Sam’s hands, relieving the pressure like so many times before. “I’m having the smallest portion of food known to mankind, I need something real. I’ll come get you soon, okay?”“Okay,” Sam says, clearly happy with being Dean’s priority right now. “I’ll call Jess.”Ketch looks like he has swallowed lemons when Dean returns to the table and Dean thinks that maybe he should feel bad about how he is behaving. Ketch has after all paid a lot of money for Dean’s company over the years and he hasn’t really done anything bad, aside from sucking in bed but that’s hardly a damning character flaw, even if it is disappointing. “I’m sorry,” Dean says, gathering up his suit jacket and throwing it on. “I need to go.”“Now?” Ketch says, clearly agitated.Dean makes a face. “Yeah, sorry. My little brother needs me.”Or he needs Sammy, or maybe a bit of both, Dean isn’t about to elaborate. The point is that Dean is feeling all kinds of negative things about his situation, and Sammy feels like a fool for having sex with a woman who then went around telling her friends about it, and both brothers will feel better when they’re together.“I’m not pleased,” Ketch says grumpily, waving at Dean’s plate with his half-finished steak. “Do you know how expensive that is?”“I know, Daddy,” Dean murmurs, leaning in to kiss Ketch on his cheek. “I’m sorry.”Saying it twice doesn’t make it truer, and Ketch looks like it didn’t suffice to begin with but Dean doesn’t care right then. Instead he slips out of the restaurant, phone in hand as he checks the time, a stray thought latching onto the tail-end of what happened here. Cas would never be mad about something like this. Cas would come with Dean to check for himself that Sam is okay. And Dean would have wanted him to. ***** The sun is high in the sky when Dean drives from San Jose where he had his brunch date with Ketch over to Stanford to pick Sam up. He drums his fingers against the steering wheel, humming along to the tunes of Pink Floyd and trying his best to not feel guilty about how he treated Ketch just now.Realistically he knows he should probably feel a bit bad. Ketch has never done anything wrong, it’s just that Dean is slowly realizing he doesn’t want this life anymore. Or he doesn’t want it with certain people. But overall he doesn’t think he should feel bad because he does everything for everyone else all the fucking time and Charlie is right, when is it time for Dean? The drive is thankfully short and when Dean arrives at the dorms, Sam is already standing at the gates, looking happy. Beaming, in fact. The sight is a welcome one and Dean smiles back when Sam gets in the passenger seat.“Happy much?” he teases and Sam laughs a little.“I just really like Jess.”Dean’s spirit soars when he hears his little brother being this pleased. “So I assume she’s up for hanging out?”“She’s pumped,” Sam grins. “She said she really wants to get to know you since she knows you’re important to me.”“Because she wants to be a part of your life,” Dean concludes smugly just as he pulls out of the parking lot. “That’s great, Sammy.”“I mean, she didn’t outright say it, but…”“I know,” Dean grins too, patting Sam’s knee. “Some things don’t need saying out loud.”For a second Dean thinks about Cas and all the things he manages to say without using words. How he touches Dean, how he treats him, little things that make Dean feel so fucking loved and damnit, Dean needs to get a grip.“It’s just all going so fast…”“I’ll say,” Dean laughs at Sam’s slightly apprehensive frown. “I barely even knew she existed until like a week ago.”“You know I knew her from before,” Sam mumbles shyly. “But she just seemed too good for me. But after Ruby I thought I should take a chance. To do better. Y’know?”Dean doesn’t really want to talk about Ruby and potentially ruin the mood but he supposes it’s okay if it’s Sam bringing her up.“The experience with her was so bad she scared you right into the arms of someone you actually like?” he smiles, refusing to see similarities with his own love life because denial is a thing that’s prevalent in Dean’s mind. “Sounds like a good outcome of a bad thing. Turn it into a positive and all that jazz.”“I guess,” Sam chuckles. “I just hope things with Jess will work out.”“One step at a time, bro,” Dean says, patting Sam’s knee again. “Now where are we going first? To get her or to get food?”“Oh!” Sam exclaims and immediately starts fiddling with his phone, making Dean laugh.Yeah, he thinks as they drive over to Jess’ sorority house, it was an unprofessional move to dump Ketch like that, but it was the emotionally right one and he is happy he was selfish for once. Feels good enough that he might try it on some more, and soon. ***** In the end they pick up Jess, Dean buys them all takeout from the same burger joint Cas took him to, and then he drives them back to his apartment. That last part makes Sam nervous as all hell and Dean fucking loves watching his little brother squirm.Jess of course doesn’t think anything of it until they reach the apartment itself and she goes “woah!” and runs up to the big windows looking out over the nearby buildings. “Is this really okay?” Sam mumbles in the corner of his mouth and Dean smiles at him, going to the kitchen area with the bags of food.He knows very well why Sam is asking, since Dean has never invited anyone to his place other than Sam and Charlie, and even so he mostly goes to Charlie’s place when they hang out. He likes his apartment well enough, but it raises inevitable questions about money, questions he usually avoids with superficial acquaintances, and sometimes he doesn’t like his apartment at all and he doesn’t want anyone near it. Sometimes it feels as if it’s bought with blood money and Dean feels like a dirty whore and showing it off would be to air out his dirty laundry.And to be honest, he knows Sam doesn’t like Dean being a sugar baby to provide for them, so he supposes that’s another reason. But yes, for today, it’s okay.“You like this girl,” he says in a low voice, looking at Jess who’s still by the windows. “You like her a lot, I can tell. And if she’s important to you…” he shrugs, letting the sentence hang, referring back to Jess’ own words about him.Sam surprises him then by coming around the kitchen island and giving Dean a hug.“Thank you.”Dean is so fucking stunned he’s about to start crying but thankfully Jess interrupts.“The food smells so good I might hug you too.”Dean grins widely, pushing one of the bags over to her. “I make it a mission in life to spread good hamburgers to the people.”“And Dean wuvs hugs,” Sam says teasingly and Dean shoves him on the shoulder, rolling his eyes.“I had a shirt that said that when I was four,” he explains to Jess while Sam goes to get plates and extra napkins. “I wore it like one time.”“It was dad’s favorite picture of Dean.”“Well I am photogenic,” Dean counters, striking a pose that makes Jess laugh. “C’mon, let’s sit on the couch.”The arguably best piece of furniture in his whole apartment. If Dean was to move, he would definitely bring that.Sitting down, he frowns momentarily. Where did the thought of moving come from? Where would he even go?“This is great,” Jess says, once again unknowingly intercepting emotional thoughts. “I’m so happy you invited me,” she grabs Sam’s hand, squeezing it, and he looks all googly eyes for a moment so Dean takes it upon himself to distribute the food. “And I love meeting you, Dean.”“Same,” Dean says with a smile, to which she beams.“I gotta say, I’m both impressed and surprised about this apartment, though,” she looks around them, at all the unnecessarily expensive shit Dean has filled the apartment with simply because it seemed fit. “It must cost a fortune.”Dean shrugs. “I do alright.” He can see the question in her open expression but she seems too polite to outright ask about his job or money. Dean likes that, and decides to indulge her instead. “I work as a male—” he pauses, throwing Sam a look. Usually when people ask, Dean evades their questions or sometimes, if he’s feeling cheeky, he says he’s a male escort. Because somehow that seems better than sugar baby, supposedly because escort is a recognized job. “Assistant,” he finishes instead, making Sam look up, meeting his eyes. “I work for four wealthy men who pay me ridiculous amounts to do all kinds of things. Y’know, the kinds of men who can be CEOs but they can’t pick up their own dry cleaning.”That makes Jess laugh. “So you run around doing their errands?”“Pretty much,” he smiles and looks away from Sam, who’s still staring at him as if Dean is some great kind of puzzle that needs solving. “I’m practically a gofer.”“That sounds pretty sweet.”“It has its ups and downs,” Dean grins, unwrapping his burger.“Like falling in love with your boss but being too chicken shit to do anything about it?” Sam blurts like the little brother ass he is.Jess makes a little peeping noise and Dean throws Sam a glare, receiving a smirk in return.“Like that,” Dean mutters.“Are you really?” Jess exclaims but then seems to settle when Dean doesn’t match her energy. “Sorry. I mean, that must be hard to deal with.”Dean shrugs. “I manage. But enough about me, tell me about you. You’re a med student?”Turns out that yes, she’s aiming to become an anesthesiologist and she’s in the same year as Sam, although they don’t have any courses together. That doesn’t seem to stop them from finding time and common interests together, though, and she regales Dean with several stories of Sam’s attempts at getting her attention.“He was adorable!” She argues with laughter in her voice when Dean can’t help but laugh in Sam’s face.“It worked, didn’t it?” Sam snaps at Dean, to which Dean only laughs harder, making Jess shake her head at them, grinning.“I changed my mind,” she says, getting up. “You are both adorable. Excuse me while I go to the little girl’s room. Try not to kill each other.”“Second door on the left,” Dean says when she turns to leave and she throws him a smile. As soon as they are alone, Dean turns back to Sam. “She’s a fucking keeper, man.”“I know,” Sam mumbles, smiling. He fiddles with leftover fries for a moment, clearly thinking. “But Dee…”“What?” Dean asks when nothing follows. He drinks noisily through the straw on his Coke, making Sam throw him a look. “What?” he repeats, smirking.“Why’d you say you’re a male assistant?”All the fun runs off Dean and he puts down his drink. “Oh.” He shrugs. “I just thought, well you like this girl, right? No need to scare her off.”“Did you think I would be embarrassed?”“Aren’t you?” Dean asks bluntly, meeting Sam’s eyes head on.The counter-question clearly catches Sam off guard and his face does a weird grimace where it looks like he’s about to cry and get mad and ashamed all at the same time.They both jerk when Jess joins them and she looks at them both, confused. “Everything okay?”Sam reaches over the table and she immediately puts her hand in his. The sight makes Dean’s insides feel warm and gooey and he irrationally longs for Cas.“Jess, listen,” Sam says, tone of voice a far cry from the joking they had done just minutes ago.“What happened?” she asks when Sam looks at Dean. “How long was I gone?”“It’s just…” Sam turns back to Jess and Dean feels uneasy. He likes this girl and he knows Sam will definitely come to love her if he gets the chance. He doesn’t want that ruined just because Sam feels like he has to be transparent about everything right away.“Sam, don’t,” Dean mumbles.“I know we haven’t known each other that long,” Sam continues, looking at Jess and ignoring Dean. “And we’ve dated even less.”Jess looks pleased as pie at the dating part. “Go on.”“You’re important to me,” Sam says confidently, voice hitching only once. Dean is so proud and apprehensive at the same time. “So I wanna be honest. Because if we’re to, like, build something…”And right there is where his voice and brain falters. What he’s saying catches up to him and his whole face turns red, something Dean definitely will tease him about later. For now he tries to think how he can slip out of the room without being seen. Or maybe no one will notice him? Jess is after all staring right at Sam with the widest grin Dean has seen this side of a Halloween pumpkin.“You wanna build something with me?”“I do,” Sam squeaks, hand trembling.Jess puts her other hand over their joined ones, leaning over the table. “I do too. Tell me what you wanna be honest about, Sammy.”Oh so she gets to call him Sammy too? Now Dean knows this is serious.“It’s about me,” he interrupts. “I lied about my job, sorry.”Sam looks like a great weight was just lifted off his shoulders and he sighs when Jess turns to look at Dean instead.“Oh?” she blinks once. “Okay.”Dean shakes his head, smiling self-deprecatingly. “Sam is afraid you’ll… I dunno, what are you scared of exactly?”And just like that, the weight is back. Well Dean isn’t all that sorry. He tried to work around this and Sam insisted on not doing it so here we are. He can’t save his little brother every time, Dean thinks somberly.“It’s just unconventional,” Sam says lamely.“Are you scared I’d be embarrassed to be together with you?” Jess asks, sounding both curious and a little offended. “I’d hoped you knew me better than that.”“It’s not that,” Sam mumbles and then sighs again, this time with frustration. “It’s just that we’re protective of each other, me and Dean. I don’t want anyone judging him.”“I know you are,” Jess mumbles, voice soft. “You told me your mom walked out and that your dad was sick. That Dean is closer to a parent for you than your actual parents.”Dean isn’t tearing up, shut up.“You said that?” he shoves Sam on his shoulder. “Way to exaggerate.”“I wasn’t,” Sam deadpans and some asshole is definitely cutting onions or something in here.“Nah,” he mumbles, turning away to wipe his cheeks. Suddenly the world seems a little less bleak, a little less heavy. Fuck Dean wants to call Cas right now. Stupid emotions being stupid.“I won’t judge, though,” Jess says then, looking at both Dean and Sam. “I want to be in Sam’s life, and I understand that entails knowing his family and history, and I want that.” She reaches over the table but doesn’t quite reach Dean. “But if you don’t want to tell me, then you don’t have to.”“It’s nothing special,” Dean says and has to clear his throat, plastering on a smile. “It’s just that I’m a sugar baby.”A small furl appears on Jess’ brow and it’s clear she’s trying to figure out what he means. Sam pats Dean on his knee, shaking his head.“Don’t do that.”“Don’t do what?”Sam swallows, gesturing to Dean’s face. “Don’t play happy like that. I want things to be real with Jess.”Dean sighs, shaking his head. Jess, meanwhile, straightens and looks surprised as all hell.“Oh you must be good at putting on faces,” she says, clearly intrigued. “That smile looked really real.”“I’ve been doing it a long time,” Dean admits, smiling for real. “But anyway. That’s the secret. My four bosses are in fact my sugar Daddies.”“Hang on,” she holds up a hand, actually giggling a little. “I’m sorry, but it’s just that I thought a sugar baby was something you were like, in a relationship. Like, if Sam had been a little bit older than me and wealthy, he would spoil me with gifts and stuff. But we’re still in a relationship. Right?”Dean nods. “Some relationships are like that.” He wouldn’t mind that with Cas, if he’s being honest and maybe it’s about fucking time he was. “But I treat it more like a job. I have four men who are all wanting to be sugar Daddies, for different reasons, and I allow them to have me fill that role.”“I’m sorry,” Jess grins. “But why would I judge you on that? It sounds like a dream.”Dean smiles, feeling Sam’s closeness like a healing pillar in his life. “Because another word to describe what I do would be prostitution.” He watches her face fall and nods soberly. “They don’t give me only money, that’s true. One of them pays for this apartment, one pays for all my clothes, one pays for all my food, and together they chip in to pay for Sam’s tuition and to give me pocket money.”Jess nods slowly. “That’s three, though.”“What?”Sam shakes his head when Dean looks at him. He didn’t understand either.“Apartment, clothing, food,” she counts, ticking them off on her fingers. “But you said you work for four men. What does the fourth one pay for?”That’s a good question, Dean. Except the occasional gift here and there, food sometimes, and promises of taking care of Sam’s tuition if that’s what it takes to get Dean to quit and instead be Cas’ full time. Except for that, what does Dean keep Cas as a sugar Daddy for?“Yeah,” Sam says pointedly, turning to Dean. “What does Cas pay for?”“Um…”Experiencing the fact that his knees are able to sweat from nervousness was not on Dean’s bingo card for today but here we are.“Oh my god!” Jess exclaims, pointing right at Dean. “He’s the one you’re in love with!”“Really?” Sam drawls, pulling on the vowels and making Jess giggle, collapsing on the couch.“You knew,” she says accusatorily, laughing harder when Sam makes a face.“You should see what Dean looks like when Cas texts him.”“It’s nothing to see!” Dean says defensively and gets to his feet. “Anyway, thank you Jess for not being weirded out.”“Hey,” she says softly, standing as well and coming over to him to hug him tightly. “You’re taking care of your family. I would never judge that. In fact,” she pulls out and smiles lovingly at him. “I adore you for taking care of someone important to me.”They both look down at Sam, who looks surprised at the turn. “What?”“I gotta say,” Dean says, tone lamenting. “It will be nice to have someone to share the burden with.”“I imagine it can get pretty heavy.”Dean squeezes Jess once more before letting go of her. “The heaviest,” he winks at Sam’s indignant “hey!”, stepping around the couch and going for the bathroom. “But the best too, of course.”“Of course,” Jess says happily and before Dean turns away from them he sees her sitting down next to Sam, pulling him into a hug.He hears them talking in low murmurs as he walks away and thinks that yeah, maybe this went better than he could have imagined and maybe he’s fucking stoked about this. Even so, his hands are trembling when he pulls out his phone, standing in the privacy of his own bedroom and listening to the dial tone.“Dean?” Cas answers, tone surprised but also pleased, somehow. “How are you?”Dean can hear voices in the background. Not like a party but maybe a meeting? It’s Sunday though, so Dean hopes it’s alright for him to call.“Good. Sorry, did I catch you at a bad time?”“Not at all,” Cas says warmly and Dean hears the voices going lower, as if Cas is walking away from them. “I’m happy you called.”Dean doesn’t know why he called, except yes he does, shut up.“Did, um, are you at work?”“No I’m actually at Gabe’s,” Cas says and yeah, that’s definitely a door closing in the background, everything going quiet now. “He has bought a new board game and invited a few friends over.”“You’re having a board game night?” Dean asks, voice tight with emotions.“Very uncool of me, huh?” Cas chuckles and Dean feels his whole body melt. “Not very Daddy-like, I’d imagine.”“I love it,” Dean rasps, clearing his throat when Cas makes a questioning sound. “What game?”“It’s the one you were talking about, Hallow’s Fall? It seems complicated, tons of tokens and a rule book thicker than it has any right to be.”Dean grins into his empty bedroom. “Cool. No spoilers, but make nice with the minister, trust me.”“Oh yeah?”“I’m not saying more than that,” Dean laughs, feeling the hollow in his chest fill somehow. “But just saying.”“Thanks for the tip,” Cas murmurs and Dean can hear him pull in a breath as if he’s about to add something but then that door opens in the background and someone is asking for him. “Yes, yes,” Cas says to the other person. “Just a minute, okay?”“You should go,” Dean counters, trying to feel as casual as he sounds. “Just, y’know, trust the dice and remember the minister.”“I will,” there’s a certain edge to Cas’ tone and it makes Dean cradle his phone closer. “But are you sure you’re okay, Dean?”“Yeah,” Dean clears his throat again. “Yeah, no, I didn’t call for anything special or nuthin’.” “I really am happy you called,” Cas says, voice warm with affection. “And I’ll see you next week.”“Sure,” Dean mumbles, feeling that hollow expanding again. “Yeah, have fun.”The call ends on a soft note but Dean can’t help but feel lost. Why had he even called? To hear Cas’ voice? That seems plausible but to be honest this little crumb only made him long for the man even more. To be a part of his world outside of their meetings, to come to these silly board game nights with Cas.Maybe, Dean thinks as he returns to Sam and Jess, he can have that, if he just starts being honest about his feelings. And maybe, if he’s being honest with at least himself, he is reaching his breaching point.

----- CHAPTER BREAK -----

Monday morning Dean is still feeling off from his own conclusions from yesterday. The visit from Sam and Jess had ended on a high note, and Dean had happily driven them both back to their respective homes. Sam had even given Dean a tight hug before getting out of the car so yeah, Dean was feeling pretty stoked about all of that.But then when he got back to his empty apartment everything else caught up with him. His feelings for Cas, his feelings about his line of work, the realization that maybe he doesn’t think it’s as fun and carefree being a sugar baby anymore. All of that kept him awake most of the night and he’s tired when he eventually joins Crowley in his Aston Martin for their day together.That tiredness doesn’t show, of course. Dean has long since learned how to use makeup to conceal the dark circles under his eyes, and he has put on his best suit, wearing it as armor. The watch Crowley bought him glistens on his wrist and he gives his Daddy of the day a winning smile when the older man nods approvingly.“Today is a little different,” Crowley says as he pulls into traffic. “In the backseat is a portfolio for you, with a tablet.”A quick frown of confusion passes over Dean’s face but he turns immediately to retrieve the portfolio. It’s more of a satchel, if he’s being honest, but he doesn’t argue that. Instead he looks inside and indeed finds an iPad.“Fancy,” he says when he presses the power button and the screen lights up with a welcome message.“Just swipe to open,” Crowley says, waving his hand, attention on the traffic around them. “You can choose your own password if you want one.”“Okay,” Dean says questioningly. He knows they’re going to another meeting — lately that seems like it’s all he does with Crowley — but that’s the extent of his knowledge.“I thought for this meeting we’ll kick it up a notch,” Crowley says, smiling to himself. “I want you to act like a proper assistant and take notes for me.”A nervous chill goes through Dean, followed by an excited warmth that definitely lingers. “Really?” he asks, unable to keep himself leveled and probably sounding as thrilled as he feels.“Really,” Crowley says and Dean can see he’s fighting another smile. “Taking notes is important. I’m trusting you with this, Dean.”Fuck yes, Dean feels so goddamn ready for this. It’s now clear to him that what Crowley had hinted at last time they met had been exactly what Dean had hoped it was. An invitation to work for the man, not as a sugar baby, but as an actual worker. Possibly as Crowley’s assistant for real. This meeting is a test then, Dean thinks, and he will fucking excel.“I won’t let you down, Fergus,” Dean says warmly and receives a pat on his thigh. “Or should I say, Mr. Crowley?”Crowley smirks at Dean’s cheeky grin. “That would probably be for the best, yes. At least when we’re not alone.”Dean nods, fucking stoked. “So then can I ask what this meeting is about?”“Of course,” Crowley says, steering them through the morning traffic with the ease of a man who usually drives himself. Dean takes a moment to figure out the tablet and the notes app. “It’s for the housing project,” he starts and good, Dean had hoped as much. “We’re meeting with an architecture firm to discuss blueprints and plans. Get an estimate.”Dean nods, smiling to himself when he finds the notes app really user friendly. Sam should have one of these.“Architecture firm?” he asks without looking up from the app. “Are the houses going to be that fancy?”Crowley chuckles. “They’re not only used for building city landscapes and New Age structures. Most legitimate firms do a lot of regular things too. But yes,” Crowley nods when Dean looks up at him. “I do want a good name attached to this project. The result will after all reflect on me.”Makes sense, Dean thinks. Crowley never does anything that doesn’t benefit him in the end. Which is perhaps why Dean feels so great about Crowley wanting him as a proper assistant, even for a single meeting. He would never choose Dean if he didn’t think it would work out great, and that’s the ego boost Dean needs right now.“Smart,” he says, smiling. “So who did you pick?”“I have two possible firms lined up but I’m hoping for the one we’re going to now to give me a good offer. They’re the best in the market.”“Great,” Dean says and looks out the window just as they pass by the sign with the firm’s name. His face falls so fast that it actually physically hurts.Visionary Vanguard, the name of the firm Cas is currently the CEO of. Dean feels as if his life flashes before his eyes but no that’s just some clouds blowing past the sun and he needs to get a fucking grip.“I’ve had the board review Vanguard’s recent work and they are both efficient and affordable,” Crowley continues, clearly unaware of how Dean is sweating all of a sudden. “And they did everything perfectly last time I hired them. Plus I like their designs in general. They don’t overdo things.”“Great,” Dean repeats in a squeak. “But, um, are you sure I’m ready for something like this? It’s really important and stuff.”“Of course you are,” Crowley says confidently, turning his car into the guest parking area. Dean knows it very well since he has put his own car there enough times. “Why did you think I dragged you to all those other meetings?”Just like Dean has suspected then, super. To be honest, if it wasn’t for the fact that its’ Cas’ firm, Dean would still be stoked about all of this. It’s such a cool fucking thing to be handpicked like this, especially someone like him who doesn’t have a degree or any previous experience.But fuck, it’s Cas’ firm.Okay, Dean thinks as he exits the car on shaky legs, let’s think this through. Cas is the CEO, what are the chances that he will sit in on a meeting with a new potential client? Surely that’s something for the Sales department or whatever, right? But fuck, what does Gabe work as? Was he in Sales? Dean can’t remember but he thinks it’s okay even if he runs into Gabe, since he probably only knows Dean as Michael’s date who had to go home early from a party because of food poisoning. That’s fine.Yeah, Dean’s going to be fine.That false confidence works all the way until they reach the security guard. Dean of course doesn’t have his card with him but just the fact that he can see the gate where the employees swipe themselves in is enough to make him nervous all over again.Crowley of course doesn’t notice and just walks straight up to the security guard and introduces himself. The guard nods, exchanges a few polite words with Crowley while he prints visitor badges for the two of them and Dean does his best to hide behind Crowley, well aware that the guard will recognize him. He doesn’t know why but it feels like the worst thing in the world if someone says something about him and Cas, as if Dean will be caught cheating with Crowley.“Here we go,” the security guard says, handing Crowley his badge. “Fergus Crowley and Dean…” the guard frowns for the slightest second. “Winchester.”Yeah, he definitely remembers Dean’s name. For all Dean knows it was this very security guard who made Dean’s employee card to begin with.“He’s my assistant,” Crowley says, as if the guard’s hesitance is because he doesn’t understand why Dean is there. Which, to be fair, probably is the case, but for different reasons than Crowley might think.The guard looks up, right at Dean and Dean gives him the slightest of slight head shakes behind Crowley’s back. A veil of neutrality falls over the guard’s face and he hands over Dean’s badge as well.“Welcome,” he says. “Please wait by the benches and someone will be with you shortly.”He pushes a button, buzzing open the visitor gate, and Dean slinks in after Crowley, thankful that the security guard is professional enough to not say anything to their faces. He can only hope that professionalism extends to the guard’s colleagues as well but he also knows there’s nothing he can do about that. For now, he forces himself to calm down.It’s a hard fought battle, though, since he doesn’t know who will be at the meeting or who will come and pick him and Crowley up to bring them to the meeting. Irrationally, Dean imagines Meg coming sauntering down the corridor but why would she? Dean needs to get a grip. Even if Cas sees him, Dean knows he can count on him being respectful and professional. He had proven as much at the party on Saturday, after all.All until Dean messed right the fuck up and begged for Cas’ cock… Can’t fault the man for giving in then, but Dean can fault himself plenty and maybe that’s the real problem here. Realizing his own feelings is one thing, but behaving around Cas before he has had time to come to terms with those feelings is another. It would be different if they met up alone, then maybe they could talk. But right now Dean wants to do his best for this meeting, to show Crowley that he is worth the man’s time, worth a job.He breathes in and out deeply and slowly once, smiling when Crowley looks at him.“Nervous?” Crowley asks and then nods. “It’s healthy, shows that you care. But don’t worry.”Good advice, Dean thinks as a tall, blonde man with a British accent comes to collect the two of them. Dean shouldn’t worry because this is just like any other meeting he has been to with Crowley. Everything is going to be fine.And it is. It’s fine all the way up to the conference room where they are seated opposite Castiel motherfucking Novak and his team.Dean wants to die. He can’t believe Cas has managed to surprise him like this twice in almost the same amount of days. The only thing that saves Dean’s sanity is that Cas looks surprised as fuck to see Dean beside Crowley so okay, maybe this wasn’t planned on his part.It does little to calm Dean down, though, and he smiles stiffly when Crowley introduces Dean as his assistant before they begin the meeting. Crowley seems surprised to see Cas too but also pleased to have the CEO himself involved in this project.“It’s for a good cause,” Cas says and Dean is sure he’s imagining Cas avoiding to look at him. By all accounts Dean is just an insignificant assistant anyway. “I would be honored to be part of making the world a little bit better.”Knowing Cas — which Dean does, intimately — that’s not just smooth talk but something he actually believes. Whether Crowley takes his words at face value or not remains to be seen, though.The meeting itself, while interesting to Dean who is starting to feel personally involved in this housing project, contains a lot of technical jargon that passes right over Dean’s head. He does his best to take notes of everything, though, and makes up his own system for keeping tabs of who said what as the meeting progresses. All in all he thinks he’s doing well.Except that every time he looks up and accidentally catches Cas’ eyes Dean’s whole body ignites. Fuck that man for being so intelligent and handsome and so Cas. And fuck Dean’s emotions for taking a whole ass year to manifest and then just one week to barrel punch Dean in the heart. Seriously.By the end of the meeting Dean feels like a sweaty, gross mess and he has been taking notes on autopilot. He can only hope they are any good and he is annoyed with himself for letting this whole thing with Cas get to him and potentially ruin his chances of working with Crowley.All of the participants in the meeting shake hands afterwards, including Dean and Cas, and Dean’s knees almost buckle. He needs to talk to Cas soon, needs to have his Daddy close, to hold Dean and whisper sweet nothings and dirty filth. Fuck.“So,” Crowley says when they are once again alone in his Aston Martin in the parking lot. “That went well.”“You think so?” Dean asks in a small voice. “Fergus, I swear I tried my best.”“I know, I saw.” Crowley looks contemplating at Dean for a moment. “But that Novak…”“What?” Dean asks nervously, fiddling with the clasp on the satchel the tablet with the notes is in now.“Do you two have history?”Dean flails. “What? No!”A smug grin spreads over Crowley’s face. “Oh so he’s one of your other sugar Daddies, is he? Makes sense that he would want to sit in on the meeting then.”“I’m—” Dean swallows, forcing himself to calm down. No use lying to Crowley, of course. “I’m sorry if this affects your job. I should have said something.”Crowley shrugs. “It doesn’t matter to me. But it is fun to contemplate. What must he be thinking right now?”Maybe that Dean is a liar who doesn’t even need a sugar Daddy because he has a high paying job and can take care of himself and he’s a giant fraud who scams men for money?“Could be anything really,” Dean peeps.“You should probably call him,” Crowley says calmly, putting the keys in the ignition. “Wouldn’t want to let the man you’re in love with think you’re lying to him.”“Yeah—what?”That makes Crowley chuckle. “If it makes you feel any better, no you weren’t as obvious as you think. I’m just good at reading people, and I know you. And yes,” he smiles the perhaps sweetest smile Dean has ever seen on him. “I definitely think he’s in love with you too. You should talk about that.”Dean swallows over a lump. “If I do,” he mumbles, taking a breath before continuing. “If I do, I need to stop being a sugar baby for other men.”“I think you should do that anyway,” Crowley says, turning the key and revving up the engine. “It’s beneath you.”“You’re exaggerating…” Dean mumbles, eyes down.“I never exaggerate, it’s too much work,” Crowley snorts at Dean’s slanted look. “I might embellish once in a while. But I assure you I’m being serious. Why do you think I have brought you to all these meetings? I told you last time, did I?”Dean’s heart leaps and he decides to take a leap of faith along with it. “So what? You’re gonna offer me a job as your actual assistant? Give me a salary and everything? A 401K?” fuck, Dean wants that. “Then what? I move out of the apartment because I obviously can’t afford it on my own and since I’m not your sugar baby anymore I don’t get things for free. I have to work for it, get a smaller apartment, struggle to help Sam pay his tuition but feel so fucking proud of myself when I make the payments?”Dean’s heart is beating fast at the end there and he only then notices that Crowley has started driving.“Just to be clear,” Crowley starts when Dean is unable to continue. “You have been working for everything you have now too. You have struggled and succeeded. Don’t put down your own efforts.”“I want to work for you, Fergus,” Dean states, voice trembling. “Please.”Crowley nods and he looks smug as fuck, as if all of this was part of his great mastermind plan. And maybe it was, maybe he saw that Dean had more to give all the way back when he and Dean first met, in life and in love, and Crowley has enjoyed being the one to shape this diamond in the rough. Maybe Crowley will take gloating credit for helping Dean and fuck it, maybe Dean will let him. But that’s for the future to see, for now all Dean wants is a regular job and Cas as a boyfriend who occasionally spoils him and who Dean can call Daddy in bed. Can that really be so hard to accomplish?No, not if Crowley’s smirk is to be believed.“I won’t say that a stipulation is that you quit being a sugar baby,” Crowley says, stopping for a red light. “But I won’t be sad if that happens.”Dean nods. “I understand. Thank you.”“And you can stay in the apartment until you have figured things out,” Crowley adds, nodding to himself. “Budgeting on a regular salary is different from what you have been doing, and you need to prioritize if you do quit as a sugar baby.”“Thank you,” Dean says again and despite the emotional turmoil of this morning he starts feeling a much needed calm settle over him. “I promise I’ll move out as soon as I can, though.”“I expect nothing else.”“I really appreciate this, Fergus.”Crowley reaches over and strokes Dean’s cheek. “No need to get sentimental now, crumpet.” He grins suddenly, unexpectedly cheekily. “But tell me, how is it that someone as smart as you took so long to figure out you’re in love?”Dean splutters. “It’s a recent thing!”“Oh please,” Crowley snorts. “It’s been months.”“Is that why you stopped sleeping with me?” Dean squints when Crowley grins again.“I might be a selfish ass but I won’t be sleeping with someone who’s clearly in love with someone else,” he states as if it’s the most obvious thing in the world. “That said, yes, I do miss your deliciously perky little ass. I hope that Castiel Novak is worth it.”Dean clears his throat self-consciously. “I, um, yes.”“Good,” Crowley nods, turning into yet another parking lot. “Now put on your game face for meeting number two. And remember,” he winks. “You’re on the clock.”Dean’s grin is so wide his cheeks hurt. “Yes, sir.” ***** That same evening Dean is riding high on life. So much so that he almost blurts out everything when he speaks to Sammy. He does manage to contain himself a little, though, still apprehensive about being too positive when this kind of change would affect them both financially. It makes Dean nervous, something his little brother of course picked up on.“I’m just thinking about the future,” Dean said when Sam asked, mind reeling too much for him to focus enough to tell Sam about Crowley’s job off and what it might entail. “I don’t want to mess anything up.”“Don’t worry,” Sam said warmly, laughter in his voice. As if he thinks Dean is silly to worry when there is nothing to worry about, right? “Whatever happens, we’ll make it work. You and me against the world.”Dean might have felt like crying. “Right.”“And hey what’s this really about? Your undying love for Cas? Are you gonna profess it already?”Dean had ended the call very abruptly after that, not fucking ready to deal with his emotions about Cas yet. Fuck, just seeing him at the meeting had been bad enough and then, after, Cas had sent a little text asking if Dean was okay. Apologizing if he had been weird.I was just surprised, Cas wrote and Dean can’t fault the man for that.You’re fine. We’re fine, Dean wrote in response and he hasn’t heard from Cas after that.Granted it’s only been a few hours but somehow it also feels like an eternity. Everything has moved so fast this past week that Dean is still reeling. Cas saying that stuff about wanting to be Dean’s number one Daddy, Dean’s feelings abruptly surfacing, Crowley coming with his job offer, Dean accepting.It’s all too much and yet he isn’t close to being done.The dial tone is loud in Dean’s ear and he sucks on his teeth while he waits, practicing his words in his mind. Charlie once told him she does that for calls and he had laughed at her but now he gets it. It’s soothing and helps prepare him.“Hello?”Fuck that, Dean’s not prepared at all.“Hiya, Arthur,” he says, signaling that this isn’t a call between a sugar baby and their Daddy. “Do you have time?”“Not really,” Ketch says, sounding annoyed. “We’re not supposed to call.”Right, because he and Ketch mainly converse via text and emails. “I know but this is kinda urgent.”“Okay,” Ketch says and sounds very annoyed. “What?”His tone is noticeably different from when they meet up, Dean notices. Usually Ketch has a pretty superior tone with everyone else but he likes to baby Dean. Not so much now when Dean apparently has disturbed the man. Well, that doesn’t perturb Dean. In fact, it makes things easier.“Do you have time to meet with me tonight?”“Uh,” Ketch sounds affronted, which makes Dean frown. “No. Our allotted time is on Wednesday.”“I know,” Dean says and tries not to sound annoyed himself. No need for Ketch to get offended by a goddamn question. “I just have something important to discuss with you.”“Well, we’re talking right now, aren’t we?” Ketch snaps. “I have other engagements. You’re hardly the only one who occupies my time.”And that’s the moment Dean realizes that while he has multiple sugar Daddies, Ketch has multiple sugar babies and honestly, that shouldn’t come as a surprise. Dean even feels relieved.“Okay,” he says and actually smiles. “I wanted to talk about our contract. I’m terminating it.”“What?”Dean chuckles at Ketch’s sharp tone. So now he’s interested in the conversation?“Yeah, you know we have a clause in it that says either one of us can terminate the relationship without giving a reason? I’m invoking it.”“You and your clauses,” Ketch mutters and Dean knows he’s still irked by the way Dean had just walked out on him yesterday.“Yes,” Dean says softly. He’s standing by the huge windows in his apartment, one of the few things he will miss about this place. The windows and the couch, but maybe Crowley will let him take the latter with him. “I’m sorry about how I treated you but I’ve got a lot on my mind.”“Okay,” Ketch says and sounds very uninterested. “Well if you won’t be my sugar baby that’s fine, I’ve got options.”“I’m sure you do,” Dean says because he doesn’t see a reason to speak his mind. And for someone else, Ketch might be their number one Daddy. “I’m very grateful for our time together, Arthur.”“Yeah,” Ketch mutters but he does sound a little uncertain now, as if he is just now realizing this is really happening and he feels unprepared. “I guess… I guess take care now, Dean?”“You too,” Dean says, pouring all sincerity he can muster into the words.After the call ends, he feels strangely empty but also kind of ecstatic. He knows that ending contracts with sugar Daddies have left him feeling similar in the past but this feels more significant and finite. Because he isn’t ending these relationships in the hopes of making new, better ones. He’s ending them to have ended things, to start a new chapter in his life with a completely different job lined up. And he’s doing it without even knowing how Cas will react.It's exhilarating and scary at the same time and he hastens to dial the next number.Michael, in contrast to Ketch, is more than happy to meet up with Dean tonight even though they don’t have a date until later in the week. Dean even feels bad about how enthusiastic Michael is but he reminds himself as he sits down opposite Michael in the man’s favorite restaurant that this is something he needs to do. Needs to start prioritizing himself and it’s anyhow better for everyone involved now that Dean has started catching feelings for someone else.“This is a nice surprise, baby,” Michael says after the waiter has given them their drinks.“I thought you’d like it,” Dean smiles and actually has to stop himself from adding Daddy at the end there. He has been with Michael for a long time, after all.“But what are you wearing, though?” Michael adds, laughing almost nervously, as if being seen with Dean when he’s in those clothes is social suicide. “You look like Paul Bunyan and a construction worker had a son.”True enough, Dean is in jeans, a faded band shirt and a flannel thrown on for the chill. Michael’s comment makes Dean smile and he takes a sip of his beer. The cheapest one on the menu because he isn’t all that sure Michael will pay for him like usual. Dean has enough money squirreled away from all his years working as a sugar baby that he can pay for himself but he wants to be frugal where he can, considering the changes he is about to make.“I suppose it’s quite different from usual,” Dean smiles and puts a hand on the menu when Michael attempts to open it to decide what to eat. “Can we talk before we order?”Michael frowns but nods, putting his menu to the side and looking attentively at Dean. Fuck okay, maybe Dean is a little nervous this time. It was far easier doing away with Ketch, that’s for sure.“I take it you didn’t ask me here on a whim?” Michael adds when Dean spends a moment thinking.Dean sighs and leans back in his seat. “No. And I swear I had this all figured out but now I’m wondering how transparent I should be.”That certainly seems to take Michael by surprise and Dean can’t really blame him.“I would hope you’d be completely transparent,” Michael says and Dean can hear a shift in his tone of voice. It goes more business-like and that makes Dean feel calmer.Dean smiles a little. “You know that aside from you, I have other sugar Daddies,” he starts and nods when Michael does. “Well, truth be told I ended up kind of messing up a little,” he grimaces slightly at his own words. Why was this so easy when he was alone in his car on the way over here?“What do you mean?”Dean sighs again. “I fell in love,” he smiles crookedly at Michael’s shocked expression. “Yeah. I messed up really bad and went completely unprofessional and totally fell in love with my sugar Daddy. Like a chump.”Wow okay, that actually feels nice to say out loud. Michael simply stares at Dean for a moment, making Dean shrug and take another sip of his beer. It’s liberatingly good and he smiles to himself.“Oh God,” Michael mumbles eventually, pointing at himself. “Is it…?”“It’s not you.”“Oh okay,” Michael grins, making a show of being so relieved. So clearly relieved to not be the object of Dean’s desires. Yup, yup, for sure. “Good.”“Yeah.”“So you’re telling me this because…?”Dean frowns. “Well obviously I have to terminate my contracts.”“Obviously?” Michael frowns too, apparently confused, which in turn makes Dean confused as fuck. “Are you pursuing something with this man?”“I…” Dean swallows, feels all the want and need bubble up inside him. “I don’t know.”“Then what’s the problem?” Michael smiles, leaning on the table. “We all knew no real feelings were involved; we’ve all been professional about this. Well I have, I can’t speak for your other Daddies, of course.”Flashes of Dean getting absolutely wrecked by Cas while he was supposed to be working with Michael flitter past Dean’s inner mind.“Yeah,” he says weakly. “I suppose that’s right. But no, I have to do the adult thing.” He smiles, nodding at his own words. “Knowing myself I would be horrible at pretending while I have feelings for someone else. It’s better to end everything so I can figure myself out.”Michael clicks his tongue, leaning back again. “That’s a shame. We had a good thing going, Dean. I was hoping it would last a little longer.”“I know,” Dean says softly, looking fondly at Michael when he gives Dean an almost boyish look. “You should know you were one of my favorites.”That’s a bit of pandering but Dean supposes top three out of four is better than fourth place. He smiles when Michael looks pleased with himself.“Well, for what it’s worth I hope things work out for you. And please,” Michael lifts Dean’s menu, handing it to him. “Let me buy you dinner one last time.”“I’m not dumb enough to say no to that,” Dean grins and clinks his glass against Michael’s when he raises it in a silent toast.Dinner goes surprisingly smoothly after that and when Michael pulls Dean in for a kiss as they prepare to part for the night, for the last time, Dean allows it. It’s bittersweet, in a way, but when he gets back to his apartment, Dean feels good about everything.It has been a long day, made longer by everything that has happened in such a short amount of time. Hell, he hasn’t even had time to tell Sam that he’s doing this right now. He feels a twinge of remorse about that, since Sam will be the most impacted by Dean’s selfish decisions, but it’s not Sam he texts when he sits down on his couch.
10:32 p.m. [Me]:
  hey
  you up?
It doesn’t take long before he gets an answer and Dean smiles to himself as he reads.
10:34 p.m. [Cas]:
  I am. How are you, Dean?
So formal. Dean bets the lack of emojis in this text and the ones he’d received earlier in the day is because Cas still feels bad about how the meeting went. It makes him roll his eyes affectionately.
10:34 p.m. [Me]:
 tired
 it was a long day

10:34 p.m. [Cas]:
  I hear that

10:35 p.m. [Me]:
  I wanted to ask
  do you have time to meet up?

10:35 p.m. [Cas]:
  Now?
Dean’s heart flutters. Wouldn’t that be something? It feels like Cas would come running if Dean only asked him to and suddenly that’s all Dean wants. But fuck, Dean wants to do this right and not rush things.
10:36 p.m. [Me]:
  nah its too late. tomorrow?

10:37 p.m. [Cas]:
  I can do tomorrow afternoon if that works for you?
Yeah, there Dean’s heart goes again, fluttering all of the goddamn place just because Cas is so willing to fit Dean in outside of their scheduled meetings. Michael literally just did the same thing this very evening and Dean barely batted an eye.“Guess it just goes to show,” Dean mumbles to himself, smiling.
10:37 p.m. [Me]:
  perfect
  let’s text again tomorrow for the exact time
10:37 p.m. [Cas]:
  I’ll wait for you, sugar pie 💖Dean grins so widely you’d think he’s auditioning for a toothpaste commercial. No fucking way he’s getting any sleep tonight, too excited by the prospect of a great future. Better get the best out of it then, he thinks and skips over to his bedroom and the drawer filled with his toys and other goodies.

----- CHAPTER BREAK -----

For having just opened, Charlie’s internet café already has a few patrons. One who is clearly enjoying a morning coffee and a sweet treat and two who are arguing about the rules to one of the board games, even though they’re not even playing it.Luckily enough all of them are on the other end of the café from where Dean is sitting behind the counter with Charlie and Sammy. She’s smiling at Sam who’s scarfing down a chocolate concoction that surely can’t be good to have at ten in the morning, but turns abruptly to Dean before he can gather his nervous and scattered thoughts.“What’s so important it couldn’t wait until closing?” she asks, referring to how Dean had insisted they meet now and not later, even though her argument was that they would have more privacy after the café is closed to the public.But fuck, he’s meeting Cas tonight, or afternoon, or whatever. He needs to talk to his closest family first. To be honest, the fact that he has up and quit as a sugar baby without first conferring with them caught up to him last night. He’d thought he would go to sleep all peacefully after successfully completing his tasks, having a nice chat with Cas, and thoroughly fucked himself on his favorite dildo. But no. His old pal Anxiety came to visit and kept him up all night.Of course he wants to talk to Charlie and Sam and of course he wants to do that before he talks to Cas but fuck, should he have talked to them before quitting his high-paying job? His thoughts had spiraled all night and now he is high on sleep-deprivation and caffeine.“Yeah,” Sam says, barely swallowing. “You’re lucky I didn’t have classes, y’know.”“Shut up,” Dean mumbles affectionately and for perhaps the first time, Sam actually shuts his cakehole. “Listen, I need you here,” he turns to Charlie, taking her hand. “Because you are my emotional support blanket and also my rationality bunny.”“That’s disgustingly sweet,” Sam says dryly when Charlie coos at Dean.“And you,” Dean turns to his little brother. “You need to be here because I value your opinion the most. And because this directly affects you.”Sam stares at him for a stunned moment. “Damn,” he mumbles. “Right in the feels? Okay, so what’s this about?”Dean clears his throat. Is it hot in here? “Well, I—”“You’re gonna quit being a sugar baby!” Sam exclaims in a stage whisper so loud it can be heard in Texas. It draws the attention of the coffee drinker but he looks down immediately again, engaged in his book. Charlie, meanwhile, gasps so hard she makes herself cough for a moment. “You are?” she asks hoarsely, eyes round.Dean nods slowly. “I am.”“That’s great, Dee,” Sam says, putting his now empty plate to the side so that he can hug Dean. Something that both surprises and pleases Dean, who hugs his brother hard.“Is it, though?” he asks in a low tone. “It will be harder to pay your tuition.”Sam looks like that thought hadn’t even crossed his mind until now. “Oh,” he shrugs, a clear attempt at looking casual. “I’ll figure it out.”“We’ll figure it out,” Charlie interjects, smiling when both brothers look at her. “We’re family now, right? Maybe you can work a few hours here, Sam? Like, regularly.”Dean’s heart fucking aches with love and everything else sappy like that. “Really?”“That’d be awesome, Charlie,” Sam grins. “Getting paid to hang out with you? Fuck yeah.”“I’ll of course help you too,” Dean says, remembering Crowley’s words about working something out. “It’s not like I’ll leave you high and dry. I just…” he looks down, seeing Cas before his mind’s eye. “I just don’t want to be pretending to love other men anymore.”“As opposed to the man you actually love, right?” Sam asks, his tone is less teasing and more sympathetic than Dean thinks he deserves.“Is this about Cas?” Charlie nearly whispers.“Yes,” Dean says simply and then sighs when both Sam and Charlie look shocked he even admitted it. “I’ve liked him from the beginning, right? But I haven’t felt like I was, y’know…” he waves at himself.“Good enough,” Sam fills in with venom in his voice that’s clearly directed to the choice of words, or else Dean’s feelings of inferiority.“Love has nothing to do with anything like that,” Charlie says vehemently.Dean just shakes his head. “Cas said something last week,” he swallows. “About wanting to be my number one Daddy. It really fucked with my head. I—” he rubs his forehead, sighing. “It made me realize I’m in love with him and I want him as my number one Daddy but not sugar Daddy, right? Do you get what I mean?” he looks wildly at them, feeling himself flailing to catch his own emotions.Charlie and Sam, meanwhile, look like this is the least complicated complication in the history of snaggy snags.“You want him as a boyfriend,” Charlie states in a very no-nonsense tone, to which Sam nods somberly.Dean feels like he’s about to explode. “That’s insane!” he looks at them both with wide eyes. “Right?”“I think it’s awesome,” Sam states calmly. “I haven’t met him but from what you and Charlie have told me, I—”“You two talk about Cas?”Charlie smiles indulgently. “We talk about you,” she clarifies. “Because we love you, babe.”Dean splutters but Sam continues before he can say anything.“My point is that if you want my blessing, you’ve got it. And I think I can speak for Charlie too, in this case.”Charlie snaps her fingers, pointing at Sammy.“Are you sure?” Dean mumbles, feeling small and vulnerable. “Even though I don’t know what to do about tuition?”Sam shrugs. “The thing about growing up is that I’ve realized I can’t be relying on someone else to do everything for me, I gotta take responsibility myself too. And it doesn’t matter if I get the best degree or the high-paying job if I don’t have a family to share it with,” he smiles a little at Dean, just about setting off the goddamn waterworks behind Dean’s eyes.The moment stretches out for a moment and then Charlie nudges Dean. “So, what are you gonna tell your Daddies? And Cas?”Dean rubs the back of his neck nervously. “Well you see, the thing is…” he smiles as best he can. “I already told them. They took it fairly well. We did have our contracts and everything.”“No shit,” Sam says, sounding more impressed than Dean would have thought. “You move fast.”“I had momentum,” Dean ventures a grin. “I went on a meeting with Crowley and uh, it turns out it was with Cas’ architecture firm. And—yeah,” he nods when both Charlie and Sam make surprised sounds. “Yeah, it was as awkward as you might think. And worse—”“How can it get worse?” Charlie laughs.Dean shakes his head, smiling. “Cas was at the meeting too and Crowley called me out on my feelings for Cas after it was over.”“No,” Sam says, shocked.“Totally did. And a little TMI but me and Crowley haven’t exactly been…” he puts his hands together, looking shiftily to the patrons who are still in the café, still not listening to the three of them.“For how long?” Charlie asks, both of them ignoring how Sam looks like he’s fighting a blush. They’re all adults here, sex is a common enough topic.“Roughly since around Valentines,” Dean says, shrugging. “Because he noticed I was developing feelings for someone else. He’s sharp like that.”“I’d say,” Sam mumbles.“Considerate too,” Charlie adds, smiling.“He actually, uh,” Dean grins proudly. “He offered me a job as his assistant instead. That’s kinda why he kept me as a sugar baby, kinda training me to become a good assistant.”Charlie and Sam exclaim “shut up” and “that’s great” at the same time and this time it’s Charlie who hugs Dean tightly.“It’s super cool,” Dean says a little bashfully. “Like, he's a bigwig and he wants me to run his errands and whatever. He even said I can stay in the apartment a while longer, until I figure out budgeting on an actual salary and stuff.”“I’ll help with that,” Charlie says brightly. “And I’m not at all surprised he wants you for that. You’re really smart, Dean.”“Yeah, just you wait,” Sam says proudly. “In a few years you might actually work as something more than an assistant. You better listen well to everything he teaches you.”Images of Dean as an executive on a board of some company or other flashes before his eyes and fuck, he kind of wants that. Wants more than what he has allowed himself to dream for.“Thank you,” he says thickly. “Your support is all I need.”“Us and Cas, huh?” Charlie winks and Dean feels that heat creeping over him again.“Right.”“When are you meeting him?” Sam grins.Dean’s stomach squirms so hard it feels like he has to throw up or eat a whole pie. “Today,” he looks at his phone but sees no new messages from Cas since their texts this morning confirming they’re still on for today. “He’s supposed to text me when he has time.”“Oh shit,” Sam says happily. “Are you nervous?”“I’m fine.”Dean doesn’t know what, either his wobbly smile or the squeak in his voice, but something makes Sam and Charlie laugh. The sound is soothing to Dean’s scattered soul and he chuckles along anxiously. Because really, how silly. Him nervous about telling his sugar Daddy he’s quitting because he’s in love with the man? Ridiculous. ***** This time when Dean arrives at Cas’ firm it’s of course the same security guard as yesterday because fuck Dean’s life, really.“Do you always work?” Dean mutters as he swipes his employee card which thankfully still works like usual.The guard grins widely. “Maybe I’m only working when you get here.”Dean makes a face, to which the guard chuckles and there’s something in the gentle banter that makes Dean feel calmer. Truth be told, he felt much better about his life choices after his conversation with Sam and Charlie, and even better yet when he received an email with a contract for Dean to sign to become a full-fledged employee at Crowley’s company.It looked pretty standard and Dean is eager to sign it but has decided to keep it professional here, to make everything seem more legit. So instead of instantly signing off, he’d emailed Crowley back stating that he would have his lawyer look it over first but that he would get back to Crowley at the latest tomorrow.“Wouldn’t expect anything else,” Crowley responded. “And tell your brother I said hi.”That had made Dean grin widely, actually loving how Crowley obviously has done a thorough background check on Dean. He most probably did that before getting Dean as his sugar baby, knowing Crowley, but either way Dean is happy about clearly having passed.So he had been riding those highs all the way until Cas texted him and suggested Dean come to his office at 4 p.m. so that they could have a talk. That had made Dean both giddy and nervous as fuck and now here he is, riding the elevator up to Cas’ floor for perhaps the last time. Or the first in their new life together.Dean hates not knowing but he loves the prospect of a bright future and tries to focus on that. Hell, he spent the afternoon looking at affordable apartments, a search made easier now that he knows what his steady income will be, as stipulated in the contract that Sam is currently reading through. A quick Google search led Dean to believe that the salary Crowley is offering is painfully average but Dean isn’t sad about that. It’ll be steady and his in a way the money he got from his sugar Daddies never was. Besides, it’s not a bad amount and Dean thinks it’s fair for the job he will most likely be doing, especially considering his level of education.Come to think of it, he reflects as he walks down the familiar corridor of offices, his job will most likely be very similar to Meg’s. Perhaps with a tad bit more secretary aspects as Crowley seems fond of having Dean at the meetings to take notes and things like that. Maybe he should ask Meg, he thinks, how she likes her job, what she does, what’s her salary? Maybe she could even teach him a thing or two.With that in mind he puts on his most charming smile as he comes up on her little station and the look makes her arch an eyebrow.“I hope the canary tasted well, kitty,” she comments in a slight drawl, smirking. “Looking good,” she gestures to his body when he stops in front of her desk.Dean looks down at himself. He’s only in simple, but snug, jeans and a tight-fitting Henley. It’s perhaps the least like a sugar baby he has ever looked, aside from the regular clothes he wears with Charlie and Sammy, and maybe that’s the point.“Thank you,” he smiles. “I felt like being myself today.”Her eye-brow changes arch. It’s almost imperceptible but Dean has made a living for himself studying people and can’t help but notice. He has surprised and intrigued her, which in turn has surprised her yet again. A feeling she is not accustomed to, but seems to enjoy.“You’re a few minutes early,” she states then, a comment from their usual repartee. “He isn’t available yet.”Dean nods, turning to gesture to the one armchair, where early appointments are supposed to wait. A concept Dean is as of yet unfamiliar with.“I know,” he smiles. “I’ll wait here.”That seems to almost shock her and her brow draws tight instead. “Is everything okay?”Dean nods again, smiling widely. “Everything is fantastic. By the way,” he changes his mind and goes up to her desk instead, picking up a stray pen. “Do you mind if I leave my number? If we can exchange?”“Why?” she asks suspiciously, but hands him a piece of paper.“Because I’m starting a new job,” he adds his name under his phone number, just to make sure. “And if I understand things correctly, it’ll probably be similar to your job,” he straightens, pushing the paper towards her. “And I would like some pointers, if you’re able.”“From me?” she asks incredulously, looking down at the number as if to check if he’s joking.“Yeah,” Dean grins widely at her. “I might be new to this line of work but from what I have seen you’re one hell of an assistant.”She looks up at him with wide eyes. “Really?” she asks in the most innocent and girlish voice he has ever heard from her.“Really,” he says truthfully and kind of feels like hugging her.He holds back, though, only because it seems too personal. The moment is anyhow interrupted by her computer dinging softly, letting her know that the event “Winchester” is starting on Cas’ calendar. Most likely a notification she has put in, something that she probably does for most of Cas’ appointments. Something to remember, Dean thinks as he winks at her and turns to Cas’ office door.Behind him, he hears her call up Cas through the intercom and Cas says “Thank you, Ms. Masters” just as Dean enters his office.“Dean,” Cas says, sounding pleased to see him and Dean can’t help how his heart swells with affection.“Hi, Cas,” he says softly but instead of rounding Cas’ desk like he usually does, he sits down in one of the chairs in front of the desk.Cas frowns but doesn’t say anything about it. “How are you?”Dean swallows. This is okay, he’s okay. He has practiced his words, just needs to get them out in the right order. First things first.“I’m here to terminate our contract. I wish to stop being your sugar baby.”Everything Dean had planned to say after that flies out the proverbial window when Cas’ face completely falls. Dean’s throat closes when he sees the stricken, devastated look on Cas. He’s no longer Castiel Novak, architect mogul, and he’s not Daddy, the handsome devil who has Dean wrapped around his finger. He’s not even that handsome little nerd Dean first saw in Charlie’s café.He's a drowned kitten and Dean put that look on him.“Why?” Cas asks in a tight voice. “Is this about my behavior at the party? But we talked on Sunday and I thought… When you contacted me yesterday I-I was—”Dean practically flings himself at Cas’ desk, desperate to wipe that expression off his Daddy. To wipe away all the hurt and confusion.“Because I’m in love with you!” he exclaims frantically.They stare at each other for a moment, eyes wide and the air around them fucking electric or some shit.“What?”Dean inhales. “I’m in love with you,” he repeats, a smidge calmer now. “You said last week that you wanna be my number one and it fucked with my head, made me realize some repressed shit.” He shakes his head, holding up his hand when it looks like Cas wants to cut in. “I want you to be my boyfriend or whatever, maybe more. But I don’t want to be your sugar baby. I want you to be a man who I’m in a relationship with, who loves me a lot and who is my Daddy in bed because that shit’s hot, and maybe you’d buy me a present once in a while because people do that,” he swallows, looking right into Cas’ blue eyes. “But I want us to be equals. Do you understand?”Well, as equal as Dean can be with an elitist like Cas. Getting a regular job seems like a good start, anyway.“Dean…”Dean leans back, smiling, proud of himself for having said his piece. “You can of course refuse, I understand if you can’t see me as anything other than a sugar baby. But that’s how I feel anyway, and that’s why I have to terminate our contract.”Cas is up and out of his chair in the blink of an eye, coming around the desk and kneeling in front of Dean. Reaching up, he cups Dean’s face with trembling hands.“Dean,” he says again in a hushed tone. “It’s all I’ve ever wanted. Ever since we met at Charlie’s internet café. But you’ve had these walls around you and I told myself I just had to prove myself to you, and to be patient.”It feels like Dean’s heart is too big for his chest. “You’re lying…” he says hoarsely because fuck, that can’t be true, right?Cas shakes his head. “I’m not. Lord knows my patience has been tried and tested, but I know you’re worth it. Dean, I would love for us to be more than what we have been so far. I have put up with our arrangement because it was better than not having you at all,” he smiles, vulnerably and beautifully. “But if you’re ready to be more then so am I too. I just need…” he swallows, clearing his throat. “I just need you to be all mine. I can take care of all your needs, if that’s what you want. Please tell me you won’t be having any sugar Daddies on the side.”“Actually,” Dean grins proudly. “I have terminated all of my contracts. I got a job. That was, um, what I was doing here yesterday. Kinda like a test.”Cas makes a disgusted sound, hanging his head, hands falling down to Dean’s thighs. “I’m so ashamed of my behavior,” he grumbles. “That was so unprofessional of me. But I couldn’t stay away,” he looks up, eyes a brilliant shade of blue. Fuck Dean wants to kiss him and why aren’t they already? They have declared intent to expand their relationship, right? “I saw your name on the list of participants and I had to know if it was you or someone else.”Dean nods. “Yeah, I didn’t know it would be with your firm until we got here. But you have to believe me, I really didn’t have a job before. I technically still don’t, I haven’t signed any papers yet.”“You should,” Cas murmurs, reaching up to stroke Dean’s cheek. “If it’s what you want to do.”Dean nods. “I do. I think Crowley will be great to work for.”“Crowley,” Cas says, clearly tasting the word. “The same Crowley who is—was your sugar Daddy? That was him yesterday?”“Yeah, but you don’t have to worry,” Dean smiles to himself. “We haven’t had that kind of relationship in a while. He kinda realized that I was developing feelings before I realized it myself. And that those feelings didn’t include him.”“Did he now?” Cas murmurs and Dean can’t help it, he has to lean in, has to get closer to Cas. Enough talking.“Please,” he mumbles, feeling his whole body pumping with need. “Can we have said all we need to say right now? Can we discuss details later?” he puts a hand on Cas’ chest, feeling his heart thump hard. “I need you, Daddy.”Cas stands up so fast Dean can practically feel the wind. And then he’s on his feet too, pulled by Cas, by Daddy, and pushed up against Cas’ desk. They crash together, lips soft, contrasting to the way they kiss. Cas is eagerly, hotly licking into Dean’s mouth, so easily making him want to yield. And fuck does he ever.He opens his mouth and legs to his Daddy, moaning into the kisses. Cas is hugging Dean so tightly, hands on Dean’s back and hip, that they can’t move but Dean fucking loves it. Loves being cradled like this and he puts his hands on Cas’ cheeks, holding him close even when they have to pull apart to breathe.Dean is hot, the air is hot, but Cas is possibly even hotter. He looks wild, feral, and Dean thinks he might possibly come like this, just by having Cas look at him like this. Like he is the most precious piece of anything that Cas can’t wait to devour and own forever and ever.“Fuck,” he whimpers, shifting against Cas. “Shit, I-I need…”Cas nods. “Daddy knows what you need, sugar pie.”Yeah, that’s not going to help. Dean feels arousal and pleasure crash over his whole damn system and he can’t be this close to coming already, that’s so fucking stupid.“It’s different,” he moans, moving with Cas when he starts slowly grinding against Dean. “It’s better.”“I know,” Cas shushes, nose pressed against the side of Dean’s neck, breathing him in. “Because I love you, and you’ve finally allowed yourself to feel it,” he growls against Dean’s ear.It makes him jump and fuck, he is definitely leaking, the swollen head of his dick getting wet and sticking to his underwear.“It can’t only be that,” Dean protests incredulously, even though his voice is all fucking breathy and whatnot. It can be so easy, his body should be so used to sex that he should need a little bit more, right?Cas just chuckles, smiling to himself as he once again kneels in front of Dean. “I will show you what love means, sweetness,” he rumbles, clever fingers opening Dean’s jeans without Dean even registering what is happening until he is standing there with his dick out.“What?”“One for the road,” Cas winks and fucking swallows Dean whole.It makes him grunt, bucking forward harshly. Too harshly, if he had been coherent, but the chances of that flew out that goddamn window that’s apparently sucking out all kinds of things today.It just feels so fucking good inside Cas’ mouth. So hot and wet and fuck, that’s the back of his throat and Dean can’t breathe it’s so tight.“Daddy,” he moans, a hand over his mouth to at least try and keep his noises to a minimum. “Fuck, Daddy.”Cas hums, blowing Dean’s mind. Pleasure surges through him, pulling his balls tight. His legs tremble so hard he would have feared he would fall if he had been able to think about anything other than the incredible heat inside him, between them, around him.Then one of Cas’ big hands wrap around his throbbing balls and another grabs Dean’s shaking thigh, and Dean’s eyes fly open.He looks down, sees Cas looking intently up at him as he sucks Dean off and fuck, there’s just something about those eyes. The intensity in them, like nothing Dean has ever seen before. How could he have been so stupid as to not understand until Cas outright came and said it. Of course Cas is Dean’s number one Daddy.“I’m coming,” Dean rasps, voice wrecked for no fucking reason at all.Fuck his dick is so hard. It’s almost painful and yet it’s the best fucking thing ever because Cas has his lips wrapped around it, his tongue pressing and prodding, pulling everything out of Dean.Cas makes a sound at the back of his throat, something almost guttural, and then he deep-throats Dean. No fucking way Dean can stop himself then. He jackknives over Cas, pressing his face closer and shaking as he comes hard deep down Cas’ throat.“Daddy…” he whimpers and fucking hell, he can’t breathe.A tap from Cas tells Dean that shit, Cas can’t breathe for real, and he snaps upright, stumbling against the desk, sitting on the edge. Cas grins up at him, panting slightly and wiping his mouth with the back of his hand.“So much to give me, sugar pie,” he rumbles and Dean knows he needs more. Needs to take care of his Daddy, to make him cream inside, and won’t be able to rest until this fire inside him has been tended to.“Please,” he says, vulnerable as he reaches for Cas. “I want more, Daddy.”Cas groans when Dean presses close to him, one leg between Cas’ to rub against the hardness there while they kiss. Dean tastes himself, licks it off to taste Cas instead. Fuck yeah.He mewls into the kisses when Cas puts his hands on Dean’s ass, massaging. He can feel that fire inside him grow, feels his hole twitching and knows only Daddy’s cock will satisfy him.“Not here,” Cas grunts when Dean starts pawing at his belt. “I want to make you scream for me, sugar pie.” He smiles when Dean turns his best puppy eyes on him. “You know I love when you beg for me,” he strokes his thumbs over Dean’s cheekbones. “But you also know I love teasing you.”He steps away with that, going for his portfolio bag and computer, presumably to shut it down for today. Dean pouts but he’s not really upset. On the contrary he’s fucking stoked. Because Cas wants to be his boyfriend and they are going to be a couple now and Dean is going to be a productive member of society and…His body stalls and he ends up standing with his hands on his clothes, mind whirring with the implications of what has happened the last two days. And what has been said here, in this room, today.It’s Cas’ chuckle that pulls him out of the spiral and he looks up at the older man with sudden realization.“Did everything catch up to you?” Cas asks gently and helps Dean put his soft dick back in his pants.Dean squirms, pressing close and breathing in Cas’ calming scent. “It’s scary,” he mumbles and feels Cas nod.“I know. How do you think I feel?” he smiles when Dean peeks at him. “I’m finally getting everything I wanted. I’m scared to death I’ll fuck it up.”Dean pulls out, brow furrowed. “You’re exaggerating.”“I’m not,” Cas murmurs, softly. “And if you give me a chance, I’ll do my best to show it.”He leans in, kissing Dean on his forehead and somehow, despite all the kisses they have shared and that Daddy has given him, that one seems to carry so much more meaning. It’s heavy in a pleasant way, like a weighted blanket, and it lingers as Cas pulls him out of his office by his hand.Outside, they stop by Meg’s desk and she looks expectantly up at Cas, clearly not at all perturbed to see them holding hands even though Dean thinks this is perhaps the first time they have done it in such a casual way. Like a boyfriend way. Dean feels giddy.“I’ll be stepping out for the day,” Cas informs her, to which she nods. “You can do the same, Ms. Masters.”She nods again, this time smiling slightly, clearly happy to have her workday end early. “Thank you, Mr. Novak. Have a good evening.”Always so polite, at least to her boss, Dean thinks and makes a mental note to try and emulate that when he starts working for Crowley.“You too, Ms. Masters.”She nods at Dean when they walk away, smiling, and he gives her a little handwave. That’s the first time she has really smiled like that and he wonders if it’s because she has noticed a difference in his and Cas’ relationship. If it’s as noticeable as it feels to Dean. But probably not. To her, he has probably always been the boss’ bratty boyfriend. Most likely, that smile is because he complimented her before and asked for her help, and Dean likes that thought.Cas holds Dean’s hand all the way down to the garage where he has his town car parked because apparently Cas doesn’t take his limo to work. Dean can’t believe he has been Cas’ sugar baby over a year now and never knew something like that about the man. He can’t fucking wait to learn more.One thing he does know, though, is the way from Cas’ office to his apartment and this isn’t it.“Um…?” he points at the turn they were supposed to take.“We’re not going home,” Cas says, voice deliciously rumbly again. “Do you honestly think I can wait that long after what we just did?”A surge of desire goes through Dean and he grins stupidly wide. “Where to, then?”“Closest hotel,” Cas says as if that’s the most obvious choice. “Anywhere with a bed so I can properly ruin you.”Instantly that time at the rooftop party flashes through Dean’s mind and he feels his dick responding with an interested tingle.“Hurry, Daddy,” he moans, putting a hand on Cas’ inner thigh, dangerously close to his clearly hardening cock.Cas clenches his hands on the steering wheel. “Don’t you worry, sugar pie. Daddy will always take care of you.”Dean grins, for once truly believing every interpretation of those words.